Halogen Patents (Class 562/472)
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Patent number: 7385082Abstract: The invention relates to a method for the preparation of de 1,3-diphenylprop-2-en-1-one substituted on one of the two phenyl groups by a carboxyalkyloxy group or a carboxyalkylthio group.Type: GrantFiled: July 8, 2004Date of Patent: June 10, 2008Assignee: GENFITInventors: Jean-François Delhomel, Karine Caumont-Bertrand
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Publication number: 20080064748Abstract: The invention relates to substituted enaminones of Formula I and their derivatives and the discovery that these compounds modulate the effect of ?-aminobutyric acid (GABA) on the GABAA receptor complex in a therapeutically relevant fashion and may be used to ameliorate CNS disorders amenable to modulation of the GABAA receptor complex.Type: ApplicationFiled: May 5, 2005Publication date: March 13, 2008Inventors: Derk J. Hogenkamp, Timothy B.C. Johnstone, Kelvin W. Gee
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Patent number: 7323591Abstract: Therapeutic compounds, methods, and compositions are disclosed herein. These compounds have prostaglandin EP2 activity, and are useful to treat and/or prevent glaucoma and/or ocular hypertension in a mammal.Type: GrantFiled: January 4, 2007Date of Patent: January 29, 2008Assignee: Allergan, Inc.Inventors: David W. Old, Todd S. Gac, Vinh X. Ngo
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Patent number: 7301050Abstract: The invention features 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs, compositions containing them, and methods of using them as PPAR delta modulators to treat or inhibit the progression of, for example, dyslipidemia.Type: GrantFiled: September 16, 2004Date of Patent: November 27, 2007Assignee: Janssen Pharmaceutical N.V.Inventors: Gee-Hong Kuo, Rui Zhang, Aihua Wang, Alan R. DeAngelis
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Patent number: 7087644Abstract: The invention relates to compounds of formula (I) as well as the salts and stereoisomers thereof wherein the several variable groups are as defined in the specification and claims. Processes for making these materials, pharmaceutical compositions containing them, and methods for using them for treatment of cardiovascular disorders are also disclosed and claimed.Type: GrantFiled: August 31, 2000Date of Patent: August 8, 2006Assignee: Bayer AktiengesellschaftInventors: Cristina Alonso-Alija, Markus Heil, Dietmar Flubacher, Paul Naab, Josef Pernerstorfer, Johannes-Peter Stasch, Frank Wunder, Klaus Dembowsky, Elisabeth Perzborn, Elke Stahl
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Patent number: 7005538Abstract: This invention relates to novel compounds which are thyroid receptor ligands, preferably antagonists, and to methods for using such compounds in the treatment of cardiac arrhythmias, thyrotoxicosis and subclinical hyperthyrodism.Type: GrantFiled: November 16, 2000Date of Patent: February 28, 2006Assignee: Karo Bio ABInventors: Johan Malm, Chris Litten, Theresa Apelqvist, Asa Hedfors, Peter Brandt, Karin Edvinsson, Sandra Gordon
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Patent number: 6884820Abstract: Compounds of the formula where the variables have the meaning defined in the specification are capable of reducing serum glucose levels in diabetic mammals without the undesirable side effect of reducing serum thyroxine levels.Type: GrantFiled: April 3, 2003Date of Patent: April 26, 2005Assignee: Allergan, Inc.Inventors: Richard L. Beard, Haiqing Yuan, Roshantha A. Chandratratna
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Patent number: 6869967Abstract: Novel compounds of the general formula (I), the use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds and methods of treatment employing these compounds and compositions. The present compounds may be useful in the treatment and/or prevention of conditions mediated by Peroxisome Proliferator-Activated Receptors (PPAR), in particular the PPAR? suptype.Type: GrantFiled: July 18, 2002Date of Patent: March 22, 2005Assignee: Novo Nordisk A/SInventors: Lone Jeppesen, Paul Stanley Bury, John Patrick Mogensen, Ingrid Pettersson, Per Sauerberg
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Patent number: 6864287Abstract: The present invention relates to the compounds of the general formula (I) and their salts and stereoisomers for the production of medicaments for the treatment of cardiovascular disorders.Type: GrantFiled: August 31, 2000Date of Patent: March 8, 2005Assignee: Bayer AktiengesellschaftInventors: Cristina Alonso-Alija, Markus Heil, Dietmar Flubacher, Paul Naab, Johannes-Peter Stasch, Frank Wunder, Klaus Dembowsky, Elisabeth Perzborn, Elke Stahl
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Patent number: 6835848Abstract: The present invention relates to a new and industrially advantageous one-pot process for the preparation of alkyl 3-cyclopropyl amino-2-[2,4-dibromo-3-(difluoromethoxy) benzoyl]-2-propenoates of in which R represents methyl or ethyl, which are valuable intermediates for the production of highly active antibacterial quinolone medicaments.Type: GrantFiled: January 6, 2003Date of Patent: December 28, 2004Assignees: Ranbaxy Laboratories Limited, Toyama Chemical Co., Ltd.Inventors: Prosenjit Bose, Naresh Kumar, Taro Kiyoto
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Patent number: 6716877Abstract: A method for treating a patient having congestive heart failure by administering a therapeutically effective amount of 3′,3,5-triiodothyropropionic acid (TRIPROP) or 3,5,3′,5′-tetraiodothyropropionic acid (TETRAPROP). Also described is a method to lower cholesterol blood levels of a patient by administering a therapeutically effective amounts of TRIPROP or TETRAPROP.Type: GrantFiled: February 18, 2003Date of Patent: April 6, 2004Assignee: The Arizona Board of Regents on behalf of the University of ArizonaInventor: Eugene Morkin
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Patent number: 6492424Abstract: Novel glucocorticoid and thyroid receptor ligands as provided which have the general formula (I): in which R1 is an aliphatic hydrocarbon, an aromatic hydrocarbon, carboxylic acid or ester thereof, alkenyl carboxylic acid or ester thereof, hydroxy, halogen, or cyano, or a pharmaceutically acceptable salt thereof. R2 and R3 are the same or different, and are hydrogen, halogen, alkyl of 1 to 4 carbons, or cycloalkyl of 3 to 5 carbons, at least one of R2 and R3 being other than hydrogen. X is carbonyl or methylene. R4 is an aliphatic, aromatic or heteroaromatic. Y is hydroxyl, methoxy, amino, or alkyl amino. n is an integer from 0 to 4. A method for treating diseases associated with metabolism dysfunction or which are dependent on the expression of a glucocorticoid or thyroid receptor gene such as diabetes, hypercholesterolemia, or obesity using these compounds is also disclosed.Type: GrantFiled: April 9, 2001Date of Patent: December 10, 2002Assignee: Karo Bio ABInventors: Theresa Apelqvist, Patrick Goede, Erik Holmgren
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Patent number: 6337306Abstract: Phenoxyacetic acid derivatives of the formula: wherein R1, R2, Xn and A are as defined herein, and a process for preparing the derivatives. The derivatives are used as herbicides.Type: GrantFiled: November 5, 1999Date of Patent: January 8, 2002Assignee: Rhone-Poulenc AgroInventors: Norio Sasaki, Atsushi Go, Hideshi Mukaida, Yukiko Oe
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Patent number: 6316666Abstract: A method for producing phenylenedioxydiacetic acids of high purity at high yield from crude phenylenedioxydiacetic acids which mainly contains phenylenedioxydiacetic acids represented by the following general formula (I): wherein, R represents a hologen, carboxyl group or hydrocarbon group having 1-4 carbon atoms, and n represents an integer from 0 to 3, wherein an alkaline aqueous solution of the crude phenylenedioxydiacetic acids is mixed with a mineral acid to precipitate the phenylenedioxydiacetic acids, wherein at least 10% by weight of the alkaline aqueous solution is mixed with a mineral acid at 0 to 50° C.; and, after completion of the mixing, the temperature of the mixture is kept at 80 to 110° C.Type: GrantFiled: February 2, 2000Date of Patent: November 13, 2001Assignee: Sumitomo Chemical Company, Ltd.Inventors: Junji Morimoto, Takashi Kamikawa, Hiroshi Ueda
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Patent number: 6274385Abstract: The present invention relates to a process of coding and identifying individual members of a chemical combinatorial library synthesized on a plurality of solid supports which undergo mix and split synthesis. The process provides for tagging the solid supports with a coding identifier that is attached to the solid support and which can be decoded by infrared or raman spectroscopy when directly attached to the support.Type: GrantFiled: August 9, 1999Date of Patent: August 14, 2001Assignee: Abbott LaboratoriesInventors: Jill Edie Hochlowski, Thomas J. Sowin, Daniel W. Norbeck, Anne-Laure Marie Grillot, Rolf E. Swenson
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Patent number: 6093799Abstract: A substrate for solid phase synthesis of the formula: ##STR1## is disclosed. Also disclosed are processes for preparing the substrate and intermediates useful therein. Among the novel intermediates are compounds of the formula: ##STR2## wherein t is 0 or 1; n is 3-20; R is OH, an activated ester or the residue of a solid support having a plurality of amino functionalities; A is --O-- or --NH-- and Q is hydrogen or a protecting group for an amine or alcohol.Type: GrantFiled: October 20, 1999Date of Patent: July 25, 2000Assignee: Pharmacopeia, Inc.Inventors: Ge Li, Sian Louise Griffiths, Edward McDonald, Libo Xu
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Patent number: 6048895Abstract: The invention provides novel PGF analogs. In particular, the present invention relates to compounds having a structure according to the following formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, X, and Z are as defined. This invention also includes optical isomers, diastereomers and enantiomers of the formula above, and pharmaceutically-acceptable salts, biohydrolyzable amides, esters, and imides thereof.The compounds of the present invention are useful for the treatment of a variety of diseases and conditions, such as bone disorders and glaucoma. Accordingly, the invention further provides pharmaceutical compositions comprising these compounds. The invention still further provides methods of treatment for bone disorders and glaucoma using theses compounds or the compositions containing them.Type: GrantFiled: September 4, 1998Date of Patent: April 11, 2000Assignee: The Procter & Gamble CompanyInventors: John August Wos, Mitchell Anthony deLong, Jack S. Amburgey, Jr., Haiyan George Dai, Biswanath De, David Lindsey Soper
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Patent number: 6008321Abstract: A substrate for solid phase synthesis of the formula: ##STR1## is disclosed. Also disclosed are processes for preparing the substrate and intermediates useful therein. Among the novel intermediates are compounds of the formula: ##STR2## wherein t is 0 or 1; n is 3-20; R is OH, an activated ester or the residue of a solid support having a plurality of amino functionalities; A is --O-- or --NH-- and Q is hydrogen or a protecting group for an amine or alcohol.Type: GrantFiled: March 16, 1998Date of Patent: December 28, 1999Assignee: Pharmacopeia, Inc.Inventors: Ge Li, Sian Louise Griffiths, Edward McDonald, Libo Xu
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Patent number: 5985927Abstract: Medicinal products for the selective control of tumor tissue and a method for control of such tumor tissue by administration of such product to a host. The products comprise: (a) two different compounds having a pH below 7 when the compounds are present in a protonated form, such compounds having the formula set forth below and (b) a pharmaceutically acceptable inert medicinal product carrier. The compounds have the following ##STR1## wherein R.sub.1 is hydrogen or a moiety which completes an ester group or an ether group, R.sub.2 is independently selected from the group consisting of an amino group, hydroxyl, an ester group, an ether group and a halogen, and n is an integer of 1 to 4.Type: GrantFiled: February 17, 1998Date of Patent: November 16, 1999Inventor: Werner Kreutz
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Patent number: 5985920Abstract: A fluorine-containing prostaglandin derivative of the formula (1) (or a salt thereof) and a medicine containing it, particularly, a preventive or therapeutic medicine for an eye disease: ##STR1## wherein A is a vinylene group or the like, R.sup.1 is an aryloxyalkyl group or the like, R.sup.2 and R.sup.3 are hydrogen atoms or the like, and Z is OR.sup.4 (wherein OR.sup.4 is a hydrogen atom or an alkyl group) or the like.Type: GrantFiled: August 3, 1998Date of Patent: November 16, 1999Assignees: Asahi Glass Company Ltd., Santen Pharmaceutical Co., Ltd.Inventors: Eiichi Shirasawa, Masaaki Kageyama, Tadashi Nakajima, Takashi Nakano, Nobuaki Mori, Hideshi Sasakura, Yasushi Matsumura, Yoshitomi Morizawa
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Patent number: 5766610Abstract: Novel pharmaceutically/cosmetically-active polycyclic aromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(e): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: April 26, 1995Date of Patent: June 16, 1998Assignee: Centre International De Recherches Dermatologiques GaldermaInventor: Jean-Michel Bernardon
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Patent number: 5512595Abstract: New substituted phenoxyisobutyric acids and esters that can be used as medicaments and correspond to the formula: ##STR1## wherein X, A, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and Z are as defined in the description.Those compounds and their physiologically tolerable salts can be used therapeutically.Type: GrantFiled: April 19, 1994Date of Patent: April 30, 1996Assignee: Adir et CompagnieInventors: Gilbert Regnier, Claude Guillonneau, Jean-Paul Vilaine, Albert Lenaers, Christine Breugnot
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Patent number: 5453443Abstract: Compounds having the formula I: ##STR1## are inhibitors of the PLA.sub.2 s enzymes. These compounds are useful as anti-allergic, anti-asthmatic, they are also useful in treating various inflammatory diseases such as rheumatoid arthritis, osteoarthritis, bursitis, psoriasis; immunoinflammatory disorders such as contact dermatitis, irritable bowel disease and the like.Type: GrantFiled: July 20, 1994Date of Patent: September 26, 1995Assignee: Merck Frosst Canada, Inc.Inventors: Helene Perrier, Petpiboon Prasit, Ian Street, Zhaoyin Wang
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Patent number: 5332857Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.Type: GrantFiled: July 6, 1992Date of Patent: July 26, 1994Assignee: Pfizer Inc.Inventors: Peter A. McCarthy, Frederick J. Walker
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Patent number: 5290812Abstract: Phenoxyalkylcarboxylic acid derivatives represented by the following formula (I) ##STR1## having a strong and selective leukotriene antagonistic action and useful for prophylaxis and therapy of allergic diseases as asthma and processes of preparing the same.Type: GrantFiled: December 30, 1991Date of Patent: March 1, 1994Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Mitsuo Ohashi, Toshio Tanaka, Norihisa Ishikawa, Tetsuya Kishi
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Patent number: 5183925Abstract: The invention relates to leukotriene-B.sub.4 derivatives of formula I, ##STR1## in which n=1-10,R.sub.1 means radical CH.sub.2 OH, radical COOR.sub.4, radical CONHR.sub.5 or radical CONR.sub.6 R.sub.7,A means a cis, trans or trans, trans--CH.dbd.CH--CH.dbd.CH group or tetramethylene group,B means an alkylene group with up to 10 C atoms,D means a direct compound, oxygen, sulfur, a --C.tbd.C group or a --CH.dbd.CR.sub.8 group,B and D together mean a direct bond,R.sub.2 means a hydrogen atom or an acid radical of an organic acid with 1-15 C atoms andR.sub.3 means a hydrogen atom, an optionally substituted alkyl radical with 1-10 C atoms,a cycloalkyl radical with 3-10 C atoms, an optionally substituted aryl radical with 6-10 C atoms or a 5-6 member heterocyclic radical and if R.sub.4 means a hydrogen atom, their salts with physiologically compatible bases and their cyclodextrin clathrates, process for their production and their pharmaceutical use.Type: GrantFiled: November 19, 1990Date of Patent: February 2, 1993Assignee: Schering AktiengesellschaftInventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Rolalnd Ederdt
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Patent number: 5167696Abstract: A compound of formula (I): ##STR1## in which Ar is an optionally substituted aryl or heterocyclic ring system; W is O or NR.sup.1 where R.sup.1 is hydrogen or lower alkyl;A is .dbd.CH or >CH.sub.2 and G is .dbd.C--R.sup.2, >CR.sup.3 R.sup.4 or >C.dbd.R.sup.5 such that --G--A-- is --CR.sup.2 .dbd.CH--, where R.sup.2 is H or CR.sup.6 R.sup.7 XR.sup.8 ; or --G--A-- is CR.sup.3 R.sup.4 --CH.sub.2 where CR.sup.3 R.sup.4 is CH--CR.sup.6 R.sup.7 XR.sup.8, CH--OCR.sup.6 R.sup.7 XR.sup.8, C(R.sup.9)OCOR.sup.10, CR.sup.9 R.sup.10, C(R.sup.9)OR.sup.10, C(OR.sup.9)OR.sup.10, or CH--CH.sub.2 (CO.sub.2 R.sup.11); or --G--A-- is --CR.sup.5 --CH.sub.2 -- where R.sup.5 is .dbd.CR.sup.7 XR.sup.8, .dbd.NOCR.sup.6 R.sup.7 XR.sup.8, .dbd.NOR.sup.11 or .dbd.NOCOR.sup.11 ;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.20)CH.sub.2, or COCH.sub.2 ;n is 0, 1 or 2;R.sup.6 and R.sup.7 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.9 R.sup.10, or R.sup.6 and R.sup.Type: GrantFiled: February 7, 1991Date of Patent: December 1, 1992Assignee: Imperial Chemical Industries PLCInventors: Ewan J. T. Chrystal, John E. D. Barton, David Cartwright
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Patent number: 5166377Abstract: The invention concerns novel 4-phenyl-1,3-dioxan-5-ylalkenoic acid derivatives of the formula I having cis relative stereochemistry at positions 4 and 5 of the dioxane ring and wherein Ra and Rb are variously hydrogen, alkyl, halogenoalkyl, alkenyl, and optionally substituted aryl or arylalkyl, Rc is hydroxy, alkoxy or alkanesulphonamido, n is 1 or 2, A is ethylene or vinylene, Y is (2-5C)polymethylene optionally substituted by alkyl, and benzene ring B is optionally substituted phenyl, or, when Rc is hydroxy, a salt thereof. The acid derivatives antagonize one or more of the actions of thromboxane A.sub.2 (TXA.sub.2) and are expected to be of value in those disease conditions in which TXA.sub.2 is involved. The invention also provides pharmaceutical compositions containing an acid derivative of formula I, and processes for their chemical production.Type: GrantFiled: February 9, 1988Date of Patent: November 24, 1992Assignee: Imperial Chemical Industries PLCInventors: Andrew G. Brewster, Peter W. R. Caulkett
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Patent number: 5151545Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.Type: GrantFiled: March 27, 1990Date of Patent: September 29, 1992Assignee: Pfizer Inc.Inventors: Peter A. McCarthy, Frederick J. Walker
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Patent number: 5145992Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 can be hydrogen, alkyl, alkoxy, halo, phenyl, substituted phenyl, or hydroxy; A can be S, O or --CH.sub.2 --; and Alk is straight or branched chain alkylene, with a base in an aprotic solvent, then reacting the resulting alkoxide with a monohaloacetic acid ester to give an alkoxyacetate followed by reaction of the alkoxyacetate with a hydrogen halide, organic acid or Lewis acid in nitromethane to give the corresponding .alpha.-alkoxyacetic acid which then may be recovered or may optionally be converted to the corresponding salt by contracting the .alpha.-alkoxyacetic acid with a base.Type: GrantFiled: May 6, 1991Date of Patent: September 8, 1992Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 5098613Abstract: This invention provides benzene derivatives, pharmaceutical formulations of those derivatives, and a method of using the derivatives for the treatment of inflammation in mammals.Type: GrantFiled: July 11, 1990Date of Patent: March 24, 1992Assignee: Eli Lilly and CompanyInventors: Nancy G. Bollinger, Theodore Goodson, Jr., David K. Herron
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Patent number: 5043257Abstract: Azo dyes of the formula ##STR1## where X is alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, X' is hydrogen, alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, Y and Y' are independently of each other hydrogen or halogen, Z is hydrogen, alkyl or alkoxy or alkylthio each of 1 to 4 carbon atoms, or halogen, M is a 1-, 2- or 3-valent metal cation, ammonium or an organic ammonium compound, m is 1, 2 or 3 and n is 2 to 10, are suitable for use as image dyes in photographic silver dye bleach materials.The dyes of the invention can also be used to dye textile materials.Type: GrantFiled: December 8, 1989Date of Patent: August 27, 1991Assignee: Ilford LimitedInventors: Kurt Baettig, Gerald C. Jan
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Patent number: 5041638Abstract: An alkenoic acid derivative of the formula ##STR1## in which X and Y are identical or different and represent sulfur, sulfoxide, sulfone, an alkylene chain, --SCH.sub.2 --, or oxygen or a direct bond,W represents --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,o represents a number 1 to 5,A and B are identical or different and represent carboxyl, carboxymethylene, tetrazolyl or tetrazolylmethylene, or --CO.sub.2 R.sup.9 or --CH.sub.2 CO.sub.2 R.sup.9 or --CONR.sup.10 R.sup.11 or nitrilen represents a number 1 to 10,m represents a number 0 to 7,T and Z are identical or different and represent oxygen or a direct bond andR.sup.2, R.sup.3, R.sup.8 are identical or different and represent hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano or nitro andR.sup.9 is lower alkyl and R.sup.10 and R.sup.11 are hydrogen, lower alkyl, alkylsulfonyl or arylsulfonyl or together are an alkylene chain to form a ringand pharmaceutically acceptable salts thereof.Type: GrantFiled: May 9, 1989Date of Patent: August 20, 1991Assignee: Bayer AktiengesellschaftInventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
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Patent number: 5021602Abstract: Novel compounds have at least one perfluorocyclobutane ring and at least two functional groups suitable for forming condensation polymers. Preferably the compounds have a structures represented by Formula II: ##STR1## wherein R and R' independently represent optionally inertly substituted groups; X and X' represent any molecular structures which link R and R' with the perfluorocyclobutane ring; n and n' are the number of G and G' groups, respectively; and G and G' independently represent any reactive functional groups or any groups convertible into reactive functional groups. The compound are preferably prepared by a process of thermally dimerizing trifluorovinyl compound to form a compounds of Formula IG.sub.n --R--X--CF.dbd.CF.sub.2wherein G represents G or G' in Formula II; X represents X or X' of Formual II; and n represents n or n' of Formula II, to form a compound having a perfluorocyclobutane group.Type: GrantFiled: June 9, 1989Date of Patent: June 4, 1991Assignee: The Dow Chemical CompanyInventors: Katherine S. Clement, David A. Babb, Bobby R. Ezzell
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Patent number: 5013864Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula R--OH wherein R is alkyl, substituted alkyl, or cycloalkyl, or cycloalkyl alkyl with a base in an aprotic organic solvent to give an alkoxide followed by removal of the organic solvent and reaction of the alkoxide with a salt of a monohaloacetic acid in a polar aprotic solvent such as DMSO to give the corresponding alkoxyacetate salt which then may be recovered or may optionally be converted to the corresponding acid by contacting the alkoxy acetate salt with an acid.Type: GrantFiled: December 8, 1989Date of Patent: May 7, 1991Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, Richard A. Mueller, John S. Ng, Richard A. Partis
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Patent number: 5004832Abstract: Compounds are described of formula ##STR1## in which: Ar represents an aryl, possibly substituted;R represents a C.sub.1 -C.sub.4 alkyl;R' represents a hydroxyl, an alkoxy, an amino group possibly mono or di-alkyl substituted, or an O.sup.-- M.sup.+ group where M.sup.+ represents the cation of an alkaline metal;X represents a hydrogen, chlorine, bromine or iodine atom, a hydroxyl, or an acyloxy, alkylsulphonyloxy or arylsulphonyloxy group.The compounds of formula I can be easily transformed into alpha-arylalkanoic acids of formula ##STR2## in which Ar and R have the aforesaid meanings.Type: GrantFiled: February 6, 1989Date of Patent: April 2, 1991Assignee: Zambon S.p.A.Inventors: Graziano Castaldi, Claudio Giordano
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Patent number: 4983629Abstract: 11-Haloprostane derivatives of general Formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or a --C.tbd.C--group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.Type: GrantFiled: June 21, 1989Date of Patent: January 8, 1991Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
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Patent number: 4937379Abstract: A process is described for preparing alpha-arylalkanoic acids, which comprises preparing and subsequently rearranging ketals of formula ##STR1## (in which Ar, R, R.sub.1, R.sub.2 and R.sub.4 have the meanings given in the description).The ketals of formula II are prepared from the corresponding alpha-hydroxyketals.The rearrangement reaction is conducted under mild conditions.Type: GrantFiled: July 30, 1987Date of Patent: June 26, 1990Assignee: Zambon S.p.A.Inventors: Claudio Giordano, Marco Villa
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Patent number: 4933367Abstract: This invention relates to carboxylic acid derivatives and their use thereof. The compounds are useful in treatment of various diseases such as diabetes, prediabetic conditions, adipositas ailments or atherosclerosis.Type: GrantFiled: March 12, 1987Date of Patent: June 12, 1990Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ernst-Christian Witte, Hans-Frieder Kuhnle
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Patent number: 4917817Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; -X- denotes ##STR2## denotes a single bond, ##STR3## n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.Type: GrantFiled: July 21, 1988Date of Patent: April 17, 1990Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
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Patent number: 4870104Abstract: 11-Haloprostane derivatives of general formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH-group,B is a --CH.sub.2 --CH.sub.2 -- or trans-CH.dbd.CH-- or a --C.tbd.C-group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C-bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.Type: GrantFiled: November 12, 1986Date of Patent: September 26, 1989Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
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Patent number: 4849530Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.Type: GrantFiled: June 6, 1988Date of Patent: July 18, 1989Assignee: Rorer Pharmaceutical CorporationInventors: Gerhard Zol, Gerhard Pfarrhofer
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Patent number: 4845264Abstract: A novel phenoxycarboxylic acid of formula (I) is disclosed. The compound is effective as herbicide for eradicating broad-leaved weeds. A combination of the phenoxycarboxylic acid and a N-phosphonomethylglycine or a glufosinate which is known as a herbicide is very effective for eradicating both broad-leaved weeds and narrow-leaved weeds.Type: GrantFiled: March 1, 1988Date of Patent: July 4, 1989Assignee: Teijin LimitedInventors: Shizuo Azuma, Toshiyuki Hiramatsu, Koji Nakagawa, Yataro Ichikawa
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Patent number: 4837342Abstract: A prostacyclin analogue having the formula: ##STR1## wherein R.sup.1 is --CO.sub.2 R.sup.5 (wherein R.sup.5 is a hydrogen atom, a straight chain or branched alkyl group having from 1 to 12 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, a cycloalkyl group having from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, or one equivalent of a cation), or --CONR.sup.6 R.sup.7 (wherein each of R.sup.6 and R.sup.7 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, or R.sup.6 and R.sup.7 together with the adjacent nitrogen atom, form a 5- or 6-membered substituted or unsubstituted hetero ring which may contain a hetero atom other than said nitrogen atom); A is --CH.sub.2 CH.sub.2 CH.sub.2 --, CH.sub.2 --O--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --O--CH.sub.2 -- or --CH.dbd.CHCH.sub.2 CH.sub. 2 --; B is trans --CH.dbd.CH-- or --C.Type: GrantFiled: February 13, 1987Date of Patent: June 6, 1989Assignees: Sagami Chemical Research Center, Toa Eiyo Ltd.Inventors: Masakatsu Shibasaki, Atsuo Takahashi, Tuyoshi Aoki, Kentaro Kogi, Yozo Nishimiya, Takeshi Nara, Takashi Yamaguchi
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Patent number: 4814497Abstract: Particulate aluminum is intimately mixed with an aromatic material that contains at least one ar-halo substituent having an atomic number above 20 and at least one side-chain halo substituent having an atomic number below 20 in the presence of an aqueous alkali or alkaline earth metal hydroxide so as to effect selective removal of the ar-halo substituent.Type: GrantFiled: May 12, 1986Date of Patent: March 21, 1989Assignee: Ethyl CorporationInventor: K. Pushpananda A. Senaratne
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Patent number: 4808750Abstract: Novel fluorophenoxyphenoxypropionates and derivatives thereof possess herbicidal activity selectively in the presence of broadleaf crops. Preemergent and postemergent applications are contemplated.Type: GrantFiled: July 14, 1986Date of Patent: February 28, 1989Assignee: The Dow Chemical CompanyInventors: Richard B. Rogers, B. Clifford Gerwick, III
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Patent number: 4804777Abstract: Process for the preparation of an aryloxyacetic acid by oxidation of aryloxyethanol of the formula: ##STR1## wherein m represents 1 or 2,n represents the numeral which results from the difference between 6 and m and R either individually or independently of one another represents hydrogen, alkyl, cycloalky, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen, alkylcarbonyl, arylcarbonyl, carboxyl or nitro, or represents a benzene ring fused to the phenyl ring, in an aqueous alkaline reaction medium at a temperature in the range of 0.degree. C. to the boiling point of the reaction medium in the presence of a catalytic amount of a catalyst comprised of palladium, silver and optionally antimony, and carbon to form the corresponding alkali metal ester and contacting the alkali metal with a mineral acid.Type: GrantFiled: October 9, 1987Date of Patent: February 14, 1989Assignee: Eastman Kodak CompanyInventors: Charles E. Sumner, Jr., Eric J. Fugate
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Patent number: 4789744Abstract: A process for the effective analytical or preparative resolution of the enantiomers of 2-(4-aryloxyphenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(4-aryloxyphenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric terpene esters by reaction with an optically active terpene alcohol and separating the diastereomers of the terpene ester by liquid chromatography with a silica column.Type: GrantFiled: August 5, 1987Date of Patent: December 6, 1988Assignee: The Dow Chemical CompanyInventor: John W. Russell
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Patent number: 4789685Abstract: 9-fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.- position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.Type: GrantFiled: January 20, 1987Date of Patent: December 6, 1988Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4786731Abstract: A method for the chromatographic resolution and analysis of the enantiomers of 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric 2-amino-1-alkanol derivatives by reaction with an optically active 2-amino-1-alkanol, and analyzing the diastereomeric mixture by gas chromatography.Type: GrantFiled: August 5, 1987Date of Patent: November 22, 1988Assignee: The Dow Chemical CompanyInventor: John W. Russell