Phenazines (including Hydrogenated) Patents (Class 544/347)
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Patent number: 6150363Abstract: Dihydrophenazinecarboxylic acid derivatives of the formula (I) wherein R.sup.1 represents hydrogen, linear or branched alkyl, etc., each of R.sup.2 and R.sup.3 represents hydrogen, 3-methyl-2-butenyl, etc., and each of R.sup.4 and R.sup.5 represents hydrogen, alkyl, alkenyl, aralkyl, aryl, hydroxyl, alkoxy, aryloxy, aralkyloxy, halogen, nitro, cyano, alkylsulfonyl, arylsulfonyl, alkylcarbonyl, arylcarbonyl, etc., provided that there is no case that both of R.sup.4 and R.sup.5 are hydrogen. The dihydrophenazinecarboxylic acid derivatives are excellent in the inhibition of glutamic acid toxicity.Type: GrantFiled: June 2, 1999Date of Patent: November 21, 2000Assignee: Nippon Chemiphar Co., Ltd.Inventors: Toshihiro Takahashi, Yutaka Nomura, Haruo Seto, Kazuo Shin-ya
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Patent number: 6117869Abstract: The present invention relates to compounds of Formula I that inhibit matrix metalloproteinases and to a method of inhibiting matrix metalloproteinases using the compounds ##STR1## More particularly, the present invention relates to a method of treating diseases in which matrix metalloproteinases are involved such as multiple sclerosis, atherosclerotic plaque rupture, restenosis, aortic aneurysm, heart failure, periodontal disease, corneal ulceration, burns, decubital ulcers, chronic ulcers or wounds, cancer metastasis, tumor angiogenesis, osteoporosis, rheumatoid or osteoarthritis, renal disease, left ventricular dilatation, or other autoimmune or inflammatory diseases dependent upon tissue invasion by leukocytes.Type: GrantFiled: July 26, 1999Date of Patent: September 12, 2000Assignee: Warner-Lambert CompanyInventors: Joseph Armand Picard, Bruce David Roth, Drago Robert Sliskovic
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Patent number: 6114332Abstract: A compound which is a bis(acridinecarboxamide) or bis(phenazinecarboxamide) derivative of formula (I): ##STR1## wherein each X, which may be the same or different in a given molecule, is --CH.dbd. or --N.dbd. each of R.sub.1 to R.sub.4 which may be the same or different, H, C.sub.1 -C.sub.4 alkyl, OH, SH, NH.sub.2, C.sub.1 -C.sub.4 alkoxy, aryloxy, NHR, N(R).sub.2, SR, SO.sub.2 R wherein R is C.sub.1 -C.sub.4 alkyl, CF.sub.3, NO.sub.2 or halogen, or R.sub.1 and R.sub.2 together form a methylenedioxy group; each of R.sub.5 and R.sub.6, which may be the same or different, is H or C.sub.1 -C.sub.4 alkyl; Z is (CH.sub.2).sub.n, (CH.sub.2).sub.n O(CH.sub.2).sub.n, (CH.sub.2).sub.n N(R.sub.7)(CH.sub.2).sub.n, (CH.sub.2).sub.n N(R.sub.7)(CH.sub.2).sub.m N(R.sub.7)(CH.sub.2).sub.n or (CH.sub.2).sub.n N(CH.sub.2 CH.sub.2).sub.2 N(CH.sub.2).sub.n wherein R.sub.7 is H or C.sub.1 -C.sub.Type: GrantFiled: June 18, 1999Date of Patent: September 5, 2000Assignee: Xenova LimitedInventors: William Alexander Denny, Swarnalatha Akuritaya Gamage, Julie Ann Spicer, Bruce Charles Baguley, Graeme John Finlay
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Patent number: 6057120Abstract: The invention concerns the use of redox-active compounds for the production of detection reagents for a method for the determination of an analyte as well as reagent kits that contain these redox-active compounds. In addition new redox-active compounds are disclosed.Type: GrantFiled: September 22, 1997Date of Patent: May 2, 2000Assignee: Roche Diagnostics GmbHInventors: Dieter Heindl, Rupert Herrmann, Joachim Hones, Hans-Peter Josel, Martina Junius-Comer, Hartmut Merdes, Axel Schmidt, Ernst Selbertinger
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Patent number: 6054453Abstract: Novel .beta.-aryl-.alpha.-oxysubstituted alkylcarboxylic acids of the formula (I) and compositions containing them. ##STR1## The compounds have hypolipidemic, antihyperglycemic uses.Type: GrantFiled: January 23, 1998Date of Patent: April 25, 2000Assignees: Redd's Research Foundation, Reddy-Cheminor, Inc.Inventors: Braj Bhushan Lohray, Vidya Bhushan Lohray, Ashok Channaveerappa Bajji, Shivaramayya Kalchar, Rajagopalan Ramanujam, Ranjan Chakrabarti
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Patent number: 5998617Abstract: An improved electrochromic device, the device incorporating an electrochromic medium that comprises at least three electroactive materials having absorption spectra that add together such that the color of the electrochromic medium can be pre-selected by individually choosing the concentrations of the at least three electroactive materials. The electrochromic medium generally maintains the pre-selected perceived color throughout its normal range of voltages when used in an electrochromic device. The at least three electroactive materials include at least one electrochemically reducible material (cathodic material), at least one electrochemically oxidizable material (anodic material) and at least one additional electroactive material which may be either an anodic or cathodic material. Thus, there are always three electroactive materials present in the medium, with at least two either being anodic or cathodic materials.Type: GrantFiled: April 2, 1997Date of Patent: December 7, 1999Assignee: Gentex CorporationInventors: Ramanujan Srinivasa, Darla J. French, Rongguang Lin, Thomas F. Guarr, Harlan J. Byker, Kelvin L. Baumann, David A. Theiste
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Patent number: 5888422Abstract: Fluorinated phenanthrene derivatives of the formula (I) ##STR1## in which the symbols and indices have the following meanings: E.sup.1, E.sup.2, E.sup.3, E.sup.4, E.sup.5 and E.sup.6 are identical or different and are --N--, --CF-- or --CH--;G is --CF.sub.2 CF.sub.2 -- or --CF.dbd.CF--;R.sup.1 and R.sup.2 are, for example, alkyl or alkoxy;M.sup.1, M.sup.2, M.sup.3 and M.sup.4 are, for example, O, --CO--O--, --O--CO-- or a single bond;A.sup.1 and A.sup.2 are, for example, 1,4-phenylene or pyrimidine-2,5-diyl;m and n are zero or one, but in total are not more than one,are suitable as components of liquid-crystalline mixtures.Type: GrantFiled: December 31, 1997Date of Patent: March 30, 1999Assignee: Hoechst AktiengesellschaftInventors: Javier Manero, Rainer Wingen
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Patent number: 5817831Abstract: Aliphatic hydrocarbyl-substituted aromatic amines are prepared by reacting an aromatic amine and an aliphatic hydrocarbylating agent, such as an olefin, in the presence of a heteropolyacid catalyst such as Cs.sub.2.5 H.sub.0.5 PW.sub.12 O.sub.40, for a period of time and at a temperature sufficient to permit reaction.Type: GrantFiled: September 8, 1997Date of Patent: October 6, 1998Assignee: The Lubrizol CorporationInventors: Douglas C. Rhubright, James D. Burrington, Ping Y. Zhu
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Patent number: 5741662Abstract: The present invention provides specific binding solid phase assay methods and kits for the detection of the presence or absence of a microorganism by directly staining the microorganism and specifically capturing the stained microorganism on a solid support. The methods find particular utility in the detection of Candida. The methods may simultaneously detect the presence or absence of multiple microorganisms.Type: GrantFiled: December 18, 1995Date of Patent: April 21, 1998Assignee: Quidel CorporationInventors: Randall D. Madsen, Lorraine S. Bautista, Jan W. Pawlak, Allan D. Pronovost
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Patent number: 5710273Abstract: A complex crystal is composed of anion of triiodine and cation of a fused compound consisting essentially of at least one nitrogen atom and at least 3 aromatic fused rings. Since the complex crystal has such a stable structure, it shows excellent heat resistance and excellent moisture resisting property. Furthermore, the complex crystal has light-polarizing performance because of an arrangement of the molecular chain of iodine. Moreover, the complex crystal exhibits excellent polarization because of an interaction between the fused compound and iodine. Therefore, the complex crystal is suitable for use as light-adjusting particles of a light valve or a light-adjusting glass.Type: GrantFiled: July 25, 1996Date of Patent: January 20, 1998Assignees: Toyota Jidosha Kabushiki Kaisha, Kabushiki Kaisha Toyota Chuo KenkyushoInventors: Arimitsu Usuki, Hisato Takeuchi, Narihito Tatsuda, Akane Okada, Toshio Kurauchi, Hiromitsu Tanaka, Shinobu Okayama, Kazuo Tojima, Akio Fukui, Toshiro Okamoto
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Patent number: 5707820Abstract: A new reagent and methods for measuring the concentration of (or detecting the presence of) an analyte in a sample. The reagent includes a phenazine-containing compound and an enzyme. The phenazine-containing compound must be of sufficient type to form a semiquinoid (the color indicator) by reaction involving the enzyme, analyte, and phenazine-containing compound. Importantly, the phenazine-containing compound must be in sufficient amount to correlate the concentration of semiquinoid to the concentration of analyte in the sample or to detect the presence of the analyte in the sample. The reagent may further include a buffer and a surfactant. The reagent may be incorporated into a film and may be provided in kit form.Type: GrantFiled: February 7, 1996Date of Patent: January 13, 1998Assignee: Boehringer Mannheim CorporationInventors: Christopher D. Wilsey, Helmut Freitag
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Patent number: 5637591Abstract: Disclosed are chemical agents with unexpected antimicrobial activity against the microbes, especially Porphyromonas gingivalis, known to be important in the cause and progression of gingivitis, periodontitis, and destruction of hard and soft oral tissues leading to tooth loss. The agents have additional unexpected anticollagenase activity useful in the direct mitigation of tissue damage. The agents can be formulated to produce various compositions and dental implements useful in management of peridental diseases, particularly those involving infection with certain gram-negative anaerobes.Type: GrantFiled: June 2, 1995Date of Patent: June 10, 1997Assignee: Fuji ImmunoPharmaceuticals Corp.Inventors: Mitsunori Ono, Y.-S. Edmond Cheng, Douglas F. Marks, Jr., Hiroshi Kataguchi
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Patent number: 5607624Abstract: A process for the preparation of compounds of formula I ##STR1## wherein the general symbols are as defined in claim 1, which comprises reacting a compound of formula III ##STR2## wherein the general symbols are as defined in claim 1, with a compound of formula IV[H].sub.n --R.sub.1 (IV).Type: GrantFiled: September 12, 1994Date of Patent: March 4, 1997Assignee: Ciba-Geigy CorporationInventors: Peter Nesvadba, Samuel Evans, Ralf Schmitt
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Patent number: 5608059Abstract: Ion-sensitive compounds have the formula A.sup.2+ B.sup.2- wherein A represents a cation capable of forming a receptor-substrate complex with an anion, and B represents one or more counter anions, the cation being an anion receptor of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or R.sup.1 and R.sup.2 taken together with the atoms separating them represent the atoms necessary to complete a (2)-cryptand; and,R.sup.3 and R.sup.4 are each independently H or a lower alkyl group having from 1 to 4 carbon atoms, or R.sup.3 and R.sup.4 taken together represent an ethylene bridging group.The compounds may be used for sensing anions.Type: GrantFiled: December 19, 1994Date of Patent: March 4, 1997Assignee: Eastman Kodak CompanyInventors: Trevor J. Wear, Christopher P. Moore, Alistair J. Goulden, Paul D. Beer, Nicholas C. Fletcher
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Patent number: 5356890Abstract: The invention relates to novel S-nitroso derivatives of ACE inhibitors and to pharmaceutical compositions comprising the S-nitrosothiol derivatives of the invention together with a pharmaceutically acceptable carrier.The invention also relates to methods for treating various pathophysiological conditions including acute myocardial infarction, left ventricular dysfunction without overt heart failure, hypertension, pulmonary hypertension, congestive heart failure, angina pectoris, vascular thrombosis, Raynauds syndrome, scleroderma, toxemia of pregnancy, acute renal failure, diabetic nephropathy, and renal artery stenosis, and to methods of inhibiting ACE and effecting vasodilation comprising administering the S-nitrosothiol derivatives of the ACE inhibitors of the invention to an animal.Type: GrantFiled: February 4, 1993Date of Patent: October 18, 1994Assignee: Brigham and Women's HospitalInventors: Joseph Loscalzo, John Cooke
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Patent number: 5281709Abstract: Disclosed is the process for the preparation of dye having excellent heat- and light-resistance. The dye can preferably be employed as a colorant for heat-resistant resin materials such as polyamide, as a colorant and a charge control agent for an electrostatic image developing toner (i.e. positively chargeable toner), and as a colorant for writing ink composition having a good aging stability. The process of the present invention comprising (a) mixing crude azine dye, produced by condensation of anilines or aniline hydrochlorides with nitrobenzenes in the presence of catalysts, with organic solvents; and (b) extracting by-products from the crude azine dye mixture.Type: GrantFiled: July 15, 1991Date of Patent: January 25, 1994Assignee: Orient Chemical Industries, Ltd.Inventors: Kazutoshi Akiyama, Sadahiko Matsubara
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Patent number: 5254550Abstract: A novel prolinal derivative of the general formula: ##STR1## [wherein A represents alkylene or alkenylene group of from 1 to 8 carbon atom(s) or a saturated hydrocarbon ring of from 3 to 7 carbon atoms,R represents hydrogen atom, phenyl group, benzyl group, alkyl group of from 1 to 8 carbon atom(s) or cycloalkyl group of from 3 to 7 carbon atoms,B represents alkylene group of from 1 to 8 atom(s) unsubstituted or substituted by phenyl group or benzyl group, or a single bond,D represents carbocyclic or heterocyclic ring unsubstituted or substituted by from one to three of halogen atom, alkyl or alkoxy group of from 1 to 4 carbon atom(s), nitro group or trifluoromethyl group]posses inhibitory activity on prolyl endopeptidase, and therefore are useful for treating and/or preventing agent for amnesia.Type: GrantFiled: December 6, 1991Date of Patent: October 19, 1993Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
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Patent number: 5208332Abstract: An optical probe enables the study of enzyme activity by absorbance spectroscopy or by sensitive fluorescence methods. In particular, the probe provides the ability to monitor the activity of cytochrome P-450.sub.scc enzyme, the rate limiting enzyme for steroid biosynthesis. Located on the inner mitochondrial membrane, P-450.sub.scc catalyzes the conversion of cholesterol to pregnenolone and isocapraldehyde by sequential oxidations of the cholesterol side chain. The fluorogenic probe includes a cholesterol-like steroid linked to a chromophore through a linking group. The chromophore is selected to have little optical response when linked to the steroid substrate and an enhanced optical response when cleaved from the substrate and linking group. Thus, a fluorescent anion that can be optically detected is generated by the side-chain cleavage reaction during steroidogenesis.Type: GrantFiled: December 20, 1991Date of Patent: May 4, 1993Assignee: The United States of America as represented by the United States Department of EnergyInventors: Babetta L. Marrone, Daniel J. Simpson, Clifford J. Unkefer, Thomas W. Whaley
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Patent number: 5189188Abstract: Compounds of the general formula ##STR1## in which the symbols have the meaning given in the description, are highly suitable as color formers in recording materials based on acid developers. They give deep blue, green-blue, green, violet or red shades which have excellent sublimation and light fastness.Type: GrantFiled: October 31, 1990Date of Patent: February 23, 1993Assignee: Bayer AktiengesellschaftInventor: Udo Eckstein
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Patent number: 5011967Abstract: Bischloroformate oligomer compositions are prepared by passing phosgene into a heterogeneous aqueous-organic mixture containing at least one dihydroxyaromatic compound, with simultaneous introduction of a base at a rate to maintain a specific pH range and to produce a specific volume ratio of aqueous to organic phase. By this method, it is possible to employ a minimum amount of phosgene. The reaction may be conducted batchwise or continuously. The bischloroformate composition may be employed for the preparation of cyclic polycarbonate oligomers or linear polycarbonate, and linear polycarbonate formation may be integrated with bischloroformate composition formation in a batch or continuous process.Type: GrantFiled: December 4, 1987Date of Patent: April 30, 1991Assignee: General Electric CompanyInventors: James M. Silva, Robert A. Pyles
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Patent number: 4960886Abstract: A charge transfer complex formed between a benzoquinone derivative represented by formula ##STR1## wherein at least one of the rings A and B represents a heterocyclic ring as defined in the specification, and an electron donor, and a salt of an anion or anion radical of the benzoquinone derivative of the above formula are disclosed. The charge transfer complex and the salt are useful as electronic materials.Type: GrantFiled: December 11, 1987Date of Patent: October 2, 1990Assignees: Fuji Xerox Co., Ltd., Toshio MukaiInventors: Toshio Mukai, Yoshiro Yamashita, Takanori Suzuki
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Patent number: 4952495Abstract: Hydrolyzable substrates comprise blocked moieties which, when cleaved from the substrate during hydrolysis, provide electron transfer agents. The released electron transfer agents can be recycled between a reductant and a reducible compound that upon reduction provides a detectable species. Alternatively, they can be recycled between an oxidant and an oxidizable compound that upon oxidation provides a detectable species. These substrates are useful in analytical compositions, elements and methods for the determination of hydrolytic analytes, such as hydrolytic enzymes or biological cells containing such enzymes.Type: GrantFiled: June 8, 1987Date of Patent: August 28, 1990Assignee: Eastman Kodak CompanyInventors: Robert T. Belly, Patricia M. Scensny, Annie L. Wu, Chung-yuan Chen
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Patent number: 4943576Abstract: Substituted quinoxalyl-imidazolidine-2,4-diones, processes for their preparation, their use as medicaments and pharmaceutical preparations 5-Quinoxalyl-imidazolidine-2,4-diones of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meanings given, and physiologically tolerated salts thereof and processes for their preparation are described. The compounds inhibit aldose reductase and can be used as medicaments.Type: GrantFiled: April 22, 1988Date of Patent: July 24, 1990Assignee: Hoechst AktiengesellschaftInventors: Heiner Glombik, Roland Utz, Hans-Jochen Lang, Karl Geisen, Friedrich E. Beyhl
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Patent number: 4933377Abstract: Sulfonium and oxysulfonium salts, useful as photoinitiators, have directly attached to the sulfur atom thereof:at least one aromatic or heterocyclic aromatic substituent containing at least 14 aromatic atoms and having a removable positive hydrogen ion, said substituent exhibiting a higher energy occupied molecular orbital than at least one other substituent directly attached to said sulfur atom;and at least one substituent comprising an electron withdrawing group and exhibiting a lower energy unoccupied molecular orbital than at least one other substituent directly attached to said sulfur atom;said salt being capable, upon exposure to visible radiation, of undergoing irreversible intramolecular rearrangement to form a Bronsted acid comprising the anion of said salt and said removable positive hydrogen ion.Type: GrantFiled: February 29, 1988Date of Patent: June 12, 1990Inventors: Franklin D. Saeva, David T. Breslin
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Patent number: 4912258Abstract: Fluorinated aniline derivatives of the general formula I are described ##STR1## in which R.sup.1 represents H or (CH.sub.2).sub.n -X, n is a whole number from 1 to 3, X is H, OH, NH.sub.2, CH.sub.3 CONH, CH.sub.3 SO.sub.2 NH, SO.sub.3 H or ArSO.sub.3 H, Ar is optionally substituted arylene radical, R.sup.1 is alternatively also a --(CH.sub.2).sub.3 -- group, which is bonded to the free o-position next to the N-atom, Y is H, --O--, --NH--, --S-- or a C--C single bond, R.sup.2, in the event that Y=H, is the same as or different from R.sup.1 and means one of the radicals shown for R.sup.1, and in the event that Y is a C--C single bond or --O--, --NH-- or --S--, is an alkylene group having 1 to 3 carbon atoms linked with Y, and R.sup.3 =H, alkyl having 1 to 3 carbon atoms, OCH.sub.3, CH.sub.3 CONH, CO.sub.2 H or SO.sub.3 H.Type: GrantFiled: February 5, 1988Date of Patent: March 27, 1990Assignee: Boehringer Mannheim GmbHInventors: Hans-Georg Batz, Rupert Herrmann
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Patent number: 4904810Abstract: Aqueous bischloroformates are prepared by the reaction of a dihydroxyaromatic compound (e.g., bisphenol A) with phosgene in a substantially inert organic liquid (e.g., methylene chloride) and in the presence of an aqueous alkali metal or alkaline earth metal base, at a pH below about 8. After all solid dihydroxyaromatic compound has been consumed, the pH is raised to a higher value in the range of about 7-12, preferably 9-11, and maintained in said range until a major proportion of the unreacted phosgene has been hydrolyzed. At the same time, any monochloroformate in the product may be converted to bischloroformate.Type: GrantFiled: July 25, 1988Date of Patent: February 27, 1990Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas G. Shannon
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Patent number: 4885368Abstract: Novel radical ion salts of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are each hydrogen, methyl, ethyl, phenyl, methoxy, ethoxy, fluorine, chlorine or bromine, or R.sup.1 or R.sup.1 and R.sup.3 may furthermore be tert-butyl and/or R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4 together may in each case form a radical of the formula ##STR2## where z is 0, 1, 2 or 3, and the fused aromatic rings are unsubstituted or monosubstituted or disubstituted by chlorine, bromine, methyl and/or methoxy, M.sup.m.sym. is an m-valent alkali metal, alkaline earth metal, transition metal, tin, lead, thallium, ammonium, phosphonium, arsonium or stibonium ion, k is from 1 to 5, l is from 0.1 to 4, m is from 1 to 3, n is from 0.1 to 4, x is from 0 to 2 and y is from 0 to 6, and k, l, n, x and y may furthermore be non-integral numbers and (l+x)=n.m, are electrically conductive in the crystalline state. A number of the salts are stable at 300.degree. C. and above.Type: GrantFiled: November 23, 1987Date of Patent: December 5, 1989Assignee: BASF AktiengesellschaftInventors: Siegfried Huenig, Alexander Aumueller, Peter Erk
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Patent number: 4877824Abstract: Compounds of the formula (I) ##STR1## in which the Rs independently of one another are H, phenyl, naphthyl or C.sub.7 -C.sub.30 alkaryl and R.sup.1 is H, C.sub.1 -C.sub.8 alkyl, C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, naphthyl, C.sub.7 -C.sub.30 alkaryl or a group of the formula (II)--(CH.sub.2).sub.a --SR.sup.3 (II)R.sup.2 is C.sub.7 -C.sub.30 alkaryl, phenyl, naphthyl or phenyl containing, in the para-position, an HO or C.sub.1 -C.sub.18 alkoxy group or a group of the formulae ##STR2## or R.sup.1 and R.sup.2, together with the nitrogen atom to which they are attached, are a radical of the formula (III) ##STR3## R.sup.3 is a radical of the formulae --(CH.sub.2).sub.b --COOR.sup.6 or --(CH.sub.2).sub.2 OCOR.sup.7, a is the number 1, 2 or 3 and b is the number 1 or 2, and R.sup.4 is phenyl or a group of the formula (II), the two R.sup.5 s independently of one another are H, C.sub.1 -C.sub.24 alkyl, C.sub.5 -C.sub.12 cycloalkyl or C.sub.7 -C.sub.9 aralkyl, and R.sup.6 is H, C.sub.1 -C.Type: GrantFiled: January 25, 1989Date of Patent: October 31, 1989Assignee: Ciba-Geigy CorporationInventor: Samuel Evans
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Patent number: 4864024Abstract: A new leuco dye is capable of developing into a colored dye which has an absorption band in the near infrared region. The new leuco dye has the following formula (I): ##STR1## wherein each of R.sup.1, R.sup.2 and R.sup.3 independently is hydrogen, an alkyl group, an aralkyl group, a cycloalkyl group or an aryl group; each of X.sup.1 and X.sup.2 independently is oxygen, sulfur or --NR.sup.4 -- (R.sup.4 has the same meaning as for R.sup.1, R.sup.2 and R.sup.3); each of the rings A to E independently is benzene ring or naphthalene ring and may have one or more substituent groups; and each of R.sup.1 to R.sup.4 may have one or more substituent groups. A recording material containing the leuco dye is also disclosed.Type: GrantFiled: February 10, 1988Date of Patent: September 5, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Toru Harada
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Patent number: 4859667Abstract: Phenothiazone derivatives and analogs thereof, pharmaceutical compositions and methods of treatment are disclosed. These compounds are useful as inhibitors of mammalian leukotriene biosynthesis. As such, these compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular disorders and inflammation.Type: GrantFiled: January 14, 1987Date of Patent: August 22, 1989Assignee: Merck Frosst Canada, Inc.Inventors: Cheuk K. Lau, Christiane Yoakim, Joshua Rokach, Rejean Fortin, Yvan Guindon
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Patent number: 4845222Abstract: Pyocyanine compounds of the formula: ##STR1## wherein R.sup.1 represents one of the formula --C.sub.1-10 -alkylene-CO.sub.2 -C.sub.1-5 -alkyl;--C.sub.1-10 -alkylene-CO.sub.2 H; and ##STR2## R.sup.2 represents hydrogen or C.sub.1-2 -alkyl and R.sup.1 is attached to the 7 or 8 aromatic ring position. The compounds are useful antibiotics.Type: GrantFiled: July 29, 1987Date of Patent: July 4, 1989Assignee: Gesellschaft fur Biotechnologische Forschung mbh (GBF)Inventors: Michael Morr, Christel Kakoschke, Hsin Tsai, Rita Getzlaff
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Patent number: 4775754Abstract: Oxazine, thiazine and diazine leuco dyes are synthesized through a reaction using a dicyclohexylcarbodiimide adduct. The adducts are themselves novel compounds.Type: GrantFiled: October 7, 1987Date of Patent: October 4, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: Kim M. Vogel, Roger A. Mader
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Patent number: 4774331Abstract: A process for ortho-cyanation of phenols or phenylamines which comprises reacting a phenyl compound having hydroxy or optionally substituted amino or cyclic amino, of which ortho position is vacant, with trichloroacetonitrile, C.sub.1 -C.sub.5 alkyl thiocyanate or C.sub.6 -C.sub.12 aryl thiocyanate in the presence of a boron trihalide and treating the resultant product with an alkali is provided, and said process is useful in the synthesis of intermediates for medicinals or pesticides.Type: GrantFiled: August 21, 1987Date of Patent: September 27, 1988Assignee: Shionogi & Co., Ltd.Inventors: Makoto Adachi, Hiromu Matsumura, Tsutomu Sugasawa
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Patent number: 4711957Abstract: The disclosure deals with novel synthesis involving (a) hydrogenation of a cis-3,3-dialkyl-3,4-dihydroquinoxaline-2-one in the presence of a suitable hydrogenation catalyst, at elevated temperature and pressure, to yield a cis-3,3-dialkyl decahydroquinoxaline-2-one; (b) reaction of trans-1,2-diaminocyclohexane with acetone cyanohydrin in the presence of water to yield trans-3,3-dimethyl-decahydroquinoxaline-2-one; and (c) a reaction of 1,2-diamine with a saturated acyclic or cyclic monoketone or aldehyde and a holoform, in the presence of (i) a phase transfer catalyst (ii) an organic solvent, and (iii) solid or aqueous alkali to yield 2-keto-1,4-diazacycloalkanes. Such compounds exhibit exceptional UV light stabilizing property.Type: GrantFiled: July 18, 1981Date of Patent: December 8, 1987Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 4709031Abstract: An alkenecarboxylic acid of the formula ##STR1## in which R.sup.1 denotes hydrogen, aryl, substituted aryl or a straight-chain or cyclic, saturated or unsaturated aliphatic hydrocarbon radical, which is optionally interrupted by O, S, N, N-alkyl, N-aryl or N-aralkyl, and which is optionally substituted by hydroxyl, alkoxy, alkyl, trifluoromethyl, halogen, phenyl, alkoxycarbonyl or dialkylamino, the two alkyl radicals together with the nitrogen atom optionally forming a 5 to 7-membered ring, which optionally contains a heteroatom from the group comprising O, S, NH or N-alkyl and these aforementioned alkyl and phenyl radicals in turn optionally being substituted by halogen, trifluoromethyl, alkyl, aryl, aralkyl, alkoxy, alkylmercapto or SO.sub.2 -alkyl,R.sup.2 represents the radical CXR.sup.8, R.sup.8 having the meaning indicated for R.sup.1 and being identical to or different from R.sup.1, andX representing oxygen, sulphur or the radical NR.sup.9 R.sup.10, R.sup.9 and R.sup.Type: GrantFiled: July 11, 1986Date of Patent: November 24, 1987Assignee: Bayer AktiengesellschaftInventors: Axel Ingendoh, Horst Meyer, Bernward Garthoff
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Patent number: 4668671Abstract: This invention describes tricyclic derivatives which are useful as histamine H.sub.1 -antagonists. A particular compound of this invention is 3-[3-(pyrido[3,2-b][1,4]-benzothiazin-10-yl)propylamino]-4-(pyrid-4-ylmeth ylamino)-1,2,5-thiadiazole-1-oxide.Type: GrantFiled: April 23, 1986Date of Patent: May 26, 1987Assignee: Smith Kline & French Laboratories LimitedInventors: Andrew D. Gribble, Robert J. Ife
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Patent number: 4657909Abstract: Acids, esters, imine acids, imine esters, and imine amides derived from 6-formyl-4,7,9-trihydroxy-1-phenazinecarboxylic acid, methyl ester and from 6-formyl-4,7,9-trihydroxy-8-methyl-1-phenazinecarboxylic acid, methyl ester demonstrate antimicrobial and antineoplastic activity.A purified strain of Streptomyces galanosa, NRRL 15738, is capable of producing 6-formyl-4,7,9-trihydroxy-8-methyl-1-phenazinecarboxylic acid, methyl ester in isolable quantities from a fermentation broth containing assimilable sources of carbon and nitrogen.Type: GrantFiled: June 10, 1985Date of Patent: April 14, 1987Assignee: Warner-Lambert CompanyInventors: Christopher F. Bigge, Edward F. Elslager, James C. French, Blanche D. Graham, Gerard C. Hokanson, Stephen W. Mamber, Tim A. Smitka, Josefino B. Tunac, John H. Wilton
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Patent number: 4593097Abstract: Phenazine compounds represented by the formula: ##STR1## wherein R is a hydrogen atom, an unsubstituted or substituted lower alkanoyl group, or an unsubstituted or substituted arylcarbonyl group have antibacterial and anti-tumor activities.Some of these compounds are produced by incubation of a microorganism.Type: GrantFiled: January 30, 1984Date of Patent: June 3, 1986Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Fusao Tomita, Keiichi Takahashi, Isao Kawamoto, Kozo Asano, Makoto Morimoto, Tadashi Ashizawa, Kazuhisa Fujimoto
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Patent number: 4568675Abstract: 3,6-Dihydroxyphenazine-1-carboxylic acid, a hypotensive agent, and its production by culturing aerobically Streptomyces species A.T.C.C. No. 39460 are disclosed herein.Type: GrantFiled: December 19, 1983Date of Patent: February 4, 1986Assignee: E. R. Squibb & Sons, Inc.Inventors: Karen Bush, Dorothy S. Slusarchyk, Wen-Chih Liu
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Patent number: 4504666Abstract: Disclosed is an improvement in process for oxidizing an aromatic amine to form an aromatic amine oxide wherein a reaction mixture of the aromatic amine and a peracid is formed and maintained under non-aqueous conditions at a temperature and for a time adequate until substantially all of the aromatic amine is formed into said aromatic amine oxide. The provision for eliminating water from the reaction mixture leads to near quantitative yields of aromatic amine oxide.Type: GrantFiled: June 4, 1982Date of Patent: March 12, 1985Assignee: Sherex Chemical Company, Inc.Inventors: Gary W. Earl, Howard M. Hickman
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Patent number: 4472578Abstract: There have been prepared novel benzo[a]phenazine derivatives of the formula ##STR1## wherein R.sup.1 is hydrogen or methoxy, R.sup.2 is hydrogen, methyl, acetyl, haloacetyl or substituted aminoalkyl, and R.sup.3 is ethoxy or substituted amino. These compounds are useful as antimicrobiological agents.Type: GrantFiled: March 23, 1983Date of Patent: September 18, 1984Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Noriichi Oda, Kazuhiro Kobayashi, Isoo Ito
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Patent number: 4459407Abstract: A 1-(4-aminobenzyl)-2,3-dioxopiperazine derivative represented by the formula: ##STR1## and a salt thereof have excellent carcinostatic activity but a low toxicity. Therefore, said compounds are useful as medicines and also as intermediates.Type: GrantFiled: February 2, 1982Date of Patent: July 10, 1984Assignee: Toyama Chemical Co., Ltd.Inventors: Takako Hori, Chosaku Yoshida, Yasuo Kiba, Ryuko Takeno, Joji Nakano, Jun Nitta, Sumiko Kishimoto, Shohachi Murakami, Hisatsugu Tsuda, Isamu Saikawa
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Patent number: 4411984Abstract: A diphenylamine compound that is a precursor for a phenazine dye comprises, in an ortho position to the amine of the diphenylamine, a sulfonyldiamido group (--NHSO.sub.2 NHR) that is capable of releasing a sulfonylamine fragment upon oxidation. The diphenylamine compound upon oxidation intramolecularly cyclizes to a phenazine dye. The sulfonylamine fragment is capable of thermally releasing ammonia or an amine. The diphenylamine compound and sulfonylamine fragment are useful in imaging such as in photothermography. Ammonia or an amine thermally released from the sulfonylamine fragment enables imaging in imaging materials that are responsive to ammonia or an amine. The diphenylamine compound also generally is a silver halide developing agent.Type: GrantFiled: May 3, 1982Date of Patent: October 25, 1983Assignee: Eastman Kodak CompanyInventor: Rolf S. Gabrielsen
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Patent number: 4400510Abstract: Antibiotic A-32256 which is produced by submerged, aerobic fermentation of a Streptomyces sp. NRRL 12067. The antibiotic has shown antibacterial activity against Staphylococcus and Streptococcus and various anaerobic species. In addition, the antibiotic has shown antitrichomonas activity in vitro, as well as activity for improving ruminant feed efficency and as a mosquito larvacide.Type: GrantFiled: September 21, 1981Date of Patent: August 23, 1983Assignee: Eli Lilly and CompanyInventors: Karl H. Michel, Marvin M. Hoehn
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Patent number: 4379925Abstract: Cyclohexanone and/or cyclohexanol can be ammoxidized in the liquid phase to heterocyclic compounds by contacting the cyclohexanone and/or cyclohexanol with various oxidation catalysts in the presence of molecular oxygen and ammonia.Type: GrantFiled: October 6, 1980Date of Patent: April 12, 1983Assignee: The Standard Oil Co.Inventors: Robert K. Grasselli, Dev D. Suresh, David R. Bridgeman
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Patent number: 4377579Abstract: Amides obtained by reaction of aminotetrazole and certain optionally substituted phenazinecarboxylic acids are potent anti-allergic agents.Type: GrantFiled: December 3, 1981Date of Patent: March 22, 1983Assignee: Minnesota Mining and Manufacturing CompanyInventor: Edward H. Erickson
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Patent number: 4376859Abstract: Process for the preparation of aniline condensation dyestuffs by reacting aniline and/or an alkylaniline batchwise, in cycles or continuously with nitrobenzene, which can be substituted and/or diazoaminobenzene, with warming and in the presence of a catalyst, characterized in that the reaction mixture is worked up continuously.Type: GrantFiled: December 24, 1980Date of Patent: March 15, 1983Assignee: Bayer AktiengesellschaftInventors: Werner Maurer, Johann Zimmer
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Patent number: 4242513Abstract: Chromogenic compounds of normally colorless form are disclosed having the following structural formula: ##STR1## wherein E represents a six-membered aromatic or heterocyclic ring which may have an aromatic condensed ring and both the E ring and the condensed ring may be substituted, A represents an optionally substituted aminophenyl, indolyl, benzoindolyl, julolidinyl or kairolyl radical or the radical represented by B, and B represents a family of heterocyclic radicals. The compounds of this invention are eligible for use in pressure-sensitive and heat sensitive record materials and manifold marking systems.Type: GrantFiled: March 5, 1979Date of Patent: December 30, 1980Assignee: Appleton Papers Inc.Inventors: Troy E. Hoover, Sheldon Farber, William J. Becker
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Patent number: 4214083Abstract: Lubricating oil additives, including the calcium salts of sulfurized alkylphenols and dispersants consisting of the reaction products of halogenated polyalkylenes and heterocyclic amines, are substantially decolorized by treatment with small amounts of alkali metal hydrides in a polar solvent at 20.degree. to 120.degree. C. Color improvement is obtained at concentrations ranging from 1 to 75 parts of an alkali metal hydride per 1000 parts of additive.Type: GrantFiled: April 17, 1978Date of Patent: July 22, 1980Assignee: Texaco Inc.Inventors: John M. Larkin, William P. Cullen, Rodney L. Sung, Benjamin H. Zoleski
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Patent number: 4204065Abstract: Soft quaternary surface active agents having the formula: ##STR1## wherein >N represents a tertiary open chain or cyclic aliphatic amine; wherein >N represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.20 open chain or cyclo alkyl group, a C.sub.1 -C.sub.20 alkoxyalkyl group, a C.sub.1 -C.sub.20 acyloxyalkyl group, a C.sub.1 -C.sub.20 haloalkyl group, a C.sub.1 -C.sub.20 carboxyalkyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O--C.sub.1 -C.sub.4 alkyl group, an O--C.sub.1 -C.sub.8 acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 represents a C.sub.9 -C.sub.22 straight or branched alkyl group, a --(CH.sub.2).sub.n -- ##STR2## group, wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each selected from the group consisting of a hydrogen atom, a methyl group or an ethyl group, a C.sub.0 -C.sub.Type: GrantFiled: December 13, 1978Date of Patent: May 20, 1980Assignee: Interx Research CorporationInventor: Nicolae S. Bodor