Alicyclic Acid Moiety Containing N, S, P, B Or Halogen Patents (Class 560/125)
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Patent number: 5614522Abstract: Urea-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.Type: GrantFiled: July 24, 1995Date of Patent: March 25, 1997Assignee: G.D. Searle & Co.Inventors: John J. Talley, Kathryn L. Reed
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Patent number: 5610297Abstract: A novel class of peptide .alpha.-ketoamides useful for selectively inhibiting serine proteases, selectively inhibiting cysteine proteases, generally inhibiting all serine proteases, and generally inhibiting all cysteine proteases, having the formula M.sub.1 -AA-NH--CHR.sub.2 --CO--CO--NR.sub.3 R.sub.4, M.sub.1 -AA.sub.2 -AA.sub.1 -CO--NR.sub.3 R.sub.4, M.sub.1 -AA-AA-AA-CO--NR.sub.3 R.sub.4, M.sub.1 -AA-AA-AA-AA-CO--NR.sub.3 R.sub.4, or M.sub.1 -AA-CO--NR.sub.3 R.sub.4.Type: GrantFiled: October 6, 1995Date of Patent: March 11, 1997Assignee: Georgia Tech Research Corp.Inventor: James C. Powers
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Patent number: 5602196Abstract: Stabilisers of formula I ##STR1## wherein R.sub.1 and R.sub.2 may be C.sub.1 -C.sub.5 alkyl, the substituents R.sub.3 to R.sub.8 may be hydrogen, the variable n may be 1 or 2, and, when n is 1, A may be an alkoxy radical, and, when n is 2, A may be a diamine radical.Type: GrantFiled: November 27, 1995Date of Patent: February 11, 1997Assignee: Ciba-Geigy CorporationInventors: Bernard Gilg, Rita Pitteloud
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Patent number: 5597938Abstract: A novel process for the production of a compound represented by the formula: ##STR1## wherein Z and Z' each represents a protective group for the hydroxyl group; R.sup.1 represents a hydrogen atom or an alkyl group; R.sup.2 represents an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a group represented by the formula --B--D (in which B is an alkylene group and D is a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenoxy group or a cycloalkyl group), a substituted or unsubstituted phenyl group or a substituted or unsubstituted phenoxy group; R.sup.3 and R.sup.4 each represents a hydrogen atom, an alkyl group or an alkoxy group; R.sup.5 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a cyano group, an amino group, a hydroxyl group or a group represented by a formula --COOR.sup.8 ; R.sup.6 represents a group represented by a formula --COOR.sup.9, a cyano group, a hydroxyl group, a group represented by a formula --OCOR.sup.Type: GrantFiled: August 10, 1995Date of Patent: January 28, 1997Assignees: Taisho Pharmaceutical Co., Ltd., Fumie SatoInventor: Fumie Sato
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Patent number: 5587514Abstract: A process for the synthesis of hydroxyethylene dipeptide isosteres from .alpha.-N,N-di(protected)-amino(alkyl or substituted alkyl)methyl ketones that can be efficiently carried out on an industrial scale. The process proceeds with excellent diastereoselectivity and chemical efficiency, and can be used to prepare a wide variety of hydroxyethylene dipeptide isosteres for a variety of uses, including as HIV-1 protease inhibitors and renin inhibitors.Type: GrantFiled: November 8, 1993Date of Patent: December 24, 1996Assignee: Emory UniversityInventors: Dennis C. Liotta, Bharat R. Lagu
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Patent number: 5583248Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is alkoxycarbonyl, aralkoxycarbonyl, alkanoyl, aralkanoyl, heterocyclylcarbonyl or a group of the formula: ##STR2## R.sup.2 is alkyl, cycloalkylalkyl or aralkyl; R.sup.3 is hydrogen and R.sup.4 is hydroxy or R.sup.3 and R.sup.4 together are oxo; R.sup.5 is alkoxycarbonyl or alkylcarbamoyl; R.sup.6 and R.sup.7 together are trimethylene or tetramethylene optionally substituted by alkyl or on adjacent carbon atoms by tetramethylene; R.sup.8 is alkoxycarbonyl, aralkoxycarbonyl, alkanoyl, aroyl, aralkanoyl or heteroeyelylearbonyl; and R.sup.9 is alkyl, cycloalkyl, cycloalkylalkyl, aralkyl, cyanoalkyl, carbamoyl-alkyl, alkylthioalkyl, alkoxyalkyl or alkoxycarbonylalkyl:and pharmaceutically acceptable acid addition salts of those compounds of formula I which are basic, inhibit aspartyl proteases of viral origin and can be used in the form of medicaments for the prophylaxis or treatment of viral infections.Type: GrantFiled: April 5, 1995Date of Patent: December 10, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Joseph A. Martin, Gareth J. Thomas
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Patent number: 5569778Abstract: A process for preparing a fluorine-containing dicarbonyl compound of the formula: R.sup.1 COCFR.sup.2 COR.sup.3 in which R.sup.1 is a hydrogen atom, or a substituted or unsubstituted alkyl or aryl group; R.sup.2 is a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl or aryl group; and R.sup.3 is a hydrogen atom, or a substituted or unsubstituted alkyl, aryl, alkoxy or aryloxy group, provided that at least two of R.sup.1, R.sup.2 and R.sup.3 may together form a part of a cyclic structure with or without a hetero atom, by reacting a dicarbonyl compound of the formula: R.sup.1 COCHR.sup.2 COR.sup.3 in which R.sup.1, R.sup.2 and R.sup.3 are the same as defined above with fluorine (F.sub.2) in at least one solvent selected from the group consisting of halogenated hydrocarbons having 1 to 5 carbon atoms and nitrile compounds, or in a solvent in the presence of a salt, or an acid having pKa of 6 or less.Type: GrantFiled: April 28, 1995Date of Patent: October 29, 1996Assignee: Daikin Industries Ltd.Inventors: Teruo Umemoto, Ginjiro Tomizawa
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Patent number: 5561211Abstract: The present invention relates to blocked polyisocyanates containing at least two isocyanate groups which are reversibly blocked with a monofunctional blocking agent for isocyanate groups and at least two isocyanate groups in the form of urea groups, which may be subsequently converted to thermally stable hydantoin groups. The present invention also relates to one-component coating compositions containing these blocked polyisocyanates and compounds containing at least two isocyanate-reactive groups.Type: GrantFiled: May 23, 1995Date of Patent: October 1, 1996Assignee: Bayer CorporationInventors: Kenneth P. Yonek, Lyuba K. Gindin, Douglas A. Wicks
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Patent number: 5536723Abstract: 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: October 6, 1994Date of Patent: July 16, 1996Assignee: Brigham & Women's HospitalInventors: Joseph Loscalzo, John Cooke
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Patent number: 5523462Abstract: Cyclohexenone derivatives I ##STR1## The cyclohexenone derivatives I are suitable as herbicides and for regulating plant growth.Type: GrantFiled: April 19, 1994Date of Patent: June 4, 1996Assignee: BASF AktiengesellschaftInventors: Juergen Kast, Thomas Zierke, Matthias Bratz, Ulf Misslitz, Norbert Meyer, Andreas Landes, Wilhelm Rademacher, Karl-Otto Westphalen, Helmut Walter
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Patent number: 5502221Abstract: A process for for producing a (2R,3S)-cyclohexylnorstatine or a salt thereof is disclosed, which comprises the steps of: enantioselectively hydrogenating a 4-cyclohexyl-2-halogeno-3-oxobutyric acid ester in the presence of a ruthenium-phosphine complex to produce a 4-cyclohexyl-2-halogeno-(3R)-hydroxybutyric acid ester (2); epoxidizing the compound (2) in the presence of a base to produce a 4-cyclohexyl-(2S,3R)-epoxybutyric acid ester (3); reacting the compound (3) with a lower trialkylsilyl azide in the presence of a Lewis acid to produce a (3S)-azide-4-cyclohexyl-(2S)-substituted butyric acid ester (4); subjecting the compound (4) to hydrogenolysis to produce a (2S,3S)-cyclohexylnorstatine derivative (5); and inverting the configuration at the 2-position of the compound (5).Type: GrantFiled: May 5, 1995Date of Patent: March 26, 1996Assignee: Takasago International CorporationInventors: Noboru Sayo, Noboru Sano, Hidenori Kumobayashi
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Patent number: 5491145Abstract: Novel compound of the general formula: ##STR1## wherein R.sup.1 stands for a hydrogen atom, an optionally substituted lower alkyl group or a halogen atom; R.sup.2 and R.sup.3 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group, provided that either R.sup.2 or R.sup.3 is a hydrogen atom, the other being an optionally substituted lower alkyl group, or R.sup.2 and R.sup.3 may, taken together with the adjacent --C=C-- group, form a 5- to 7-membered ring; X stands for an oxygen atom or S(O).sub.p (p stands for an integer from 0 to 2; Y stands for a group of the formula: ##STR2## (R.sup.4 and R.sup.5 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group) or a divalent group derived from an optionally substituted 3- to 7-membered homocyclic or heterocyclic ring; R.sup.6 and R.sup.7 each stands for a hydrogen atom, an optionally substituted lower lakyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl group, or R.sup.Type: GrantFiled: November 21, 1994Date of Patent: February 13, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
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Patent number: 5491169Abstract: Compounds having the properties of morphinic substances, particularly anasia, with beneficial effects on behaviour and with peripheral effects without their major drawbacks (tolerence, addiction), the blood-brain barrier and having the following formula :H.sub.2 N--CH(R.sub.1)--CH(R.sub.2)--S--S--CH(R.sub.3)--CH(R.sub.4)--A--B--Zwherein: AB preferably represents a CO amide bond, R.sub.2 et R.sub.3 preferably represent a hydrogen atom, R.sub.1 et R.sub.4 preferably represent, independently of each other, a benzyl grouping, --CH.sub.2 CH.sub.2 SCH.sub.3, --CH.sub.2 --CH.sub.2 --S(O)--CH.sub.3 or --CH.sub.2 --CH(CH.sub.3) .sub.2, Z may represent a --CH(R.sub.5)[CH(R.sub.6)].sub.n --COO(R.sub.7) grouping wherein: R.sub.5 may represent a hydrogen atom, a methyl grouping, a benzyl grouping or a phenyl grouping, R.sub.6 may represent a hydrogen atom and may also form a hydrocarbon cycle with R.sub.5, or Z may represent a heterocyclic grouping, and preferably a morpholinyl grouping. No drawings.Type: GrantFiled: September 26, 1994Date of Patent: February 13, 1996Assignee: Institut National de la Sante et de la Recherche Medicale (INSERM)Inventors: Bernard Roques, Marie C. Fournie-Zaluski
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Patent number: 5491170Abstract: .beta.-Carboxy sulfonyl compounds of the formula ##STR1## wherein R.sub.1 is aryl, R.sub.3 is hydrogen or alkyl, R.sub.3 and R.sub.4 are hydrogen or alkyl, Y is --O--, --S--, or --NR.sub.2 --, and R.sub.5 is alkyl or aryl are potent inhibitors of the enzyme acyl CoA:cholesterol acyltransferase (ACAT) and are thus useful for treating hypercholesterolemia and atherosclerosis.Type: GrantFiled: December 19, 1994Date of Patent: February 13, 1996Assignee: Warner-Lambert CompanyInventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
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Patent number: 5489704Abstract: The present invention relates to an aldimine/aspartate corresponding to the formula ##STR1## wherein X represents an organic group which has a valency of n and is inert towards isocyanate groups at a temperature of 100.degree. C. or less,R.sub.1 and R.sub.2 may be the same or different and represent optionally substituted hydrocarbon radicals, or R.sub.1 and R.sub.2 together with the .beta.-carbon atom form a cycloaliphatic or heterocyclic ring andR.sub.3 and R.sub.4 may be identical or different and represent organic groups which are inert towards isocyanate groups at a temperature of 100.degree. C. or less,R.sub.5 and R.sub.6 may be identical or different and represent hydrogen or organic groups which are inert towards isocyanate groups at a temperature of 100.degree. C. or less, anda and b represent integers with a value of 1 to 5, provided that the sum of a and b is 2 to 6.Type: GrantFiled: August 29, 1994Date of Patent: February 6, 1996Assignees: Bayer Corporation, Bayer AktiengesellschaftInventors: Edward P. Squiller, Christian Zweiner
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Patent number: 5482947Abstract: Urea-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.Type: GrantFiled: November 15, 1993Date of Patent: January 9, 1996Inventors: John J. Talley, Daniel P. Getman, Gary A. DeCrescenzo, Ko-Chung Lin, Michael L. Vazquez, Richard A. Mueller, Kathryn L. Reed, Robert M. Heintz, Michael Clare, John N. Freskos, Eric T. Sun
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Patent number: 5481026Abstract: The invention relates to new optically active amino acid derivatives of the general formula (I) ##STR1## in which n, R, R.sub.1, R.sub.2, R.sub.3, X and A have the meaning given in the description, which amino acid derivatives contain sulphoxide or sulphone groups, to two basic synthetic routes for the preparation from sulphur-containing amino acids, to the polymerization of these monomers and to the use of the polymers as optically active adsorbents for chromatographic resolution of racemates to give the enantiomers.Type: GrantFiled: July 1, 1994Date of Patent: January 2, 1996Assignee: Bayer AktiengesellschaftInventors: Michael Grosse-Bley, Bruno Bomer, Rolf Grosser, Walter Lange, Franz-Peter Hoever, Dieter Arlt
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Patent number: 5481034Abstract: The present invention provides novel fluorinated abscisic acid derivative represented by formula of: ##STR1## wherein: X is O(CH.sub.2).sub.2 O or O; and,R is hydroxymethyl, aldehyde, C.sub.1-2 alkoxycarbonyl or carboxyl group.The present invention also provides a novel process for preparing the fluorinated abscisic acid derivative represented as the formula (I), and also provides their use for plant growth regulator.Type: GrantFiled: November 29, 1994Date of Patent: January 2, 1996Assignee: Korea Research Institute of Chemical TechnologyInventors: Bum-Tae Kim, Yong-Ki Min, No-Kyun Park, Tae-Jun Kim, Kwang-Yun Cho
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Patent number: 5476966Abstract: This invention relates to certain S-substituted homocysteine sulfoximines and their uses. Buthionine sulfoximine (BSO) appears to have significant uses for chemotherapy and radio therapy, especially combination chemotherapy and radiation therapy and for treatment of subjects with parasitic infections. The compounds of the invention have the same above-mentioned utilities as BSO but have one or more superior attributes when compared to BSO.Type: GrantFiled: January 13, 1995Date of Patent: December 19, 1995Assignee: Cornell Research Foundation, Inc.Inventors: Mary Anderson, Alton Meister
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Patent number: 5476644Abstract: The present invention provides compounds of the formula ##STR1## chelated with a paramagnetic metal ion wherein Z1 and Z2 each represent the atoms necessary to complete a monocyclic or polycyclic carbocyclic or heterocyclic ring system, said Z1 and Z2 independently optionally substituted with R.sup.6 and R.sup.7, respectively;R.sup.l, R.sup.2, R.sup.3 and R.sup.4 are independently carboxyalkyl (C.sub.1 -C.sub.2), --(CH.sub.2).sub.n --C(.dbd.O)--NH--R.sup.8, or --(CH.sub.2).sub.n --C(.dbd.O)--O--R.sup.8R.sup.5 is carboxyalkyl (C.sub.1 -C.sub.2);R.sup.6 and R.sup.7 are independently hydrogen, benzyl, or benzyloxy, said benzyl or benzyloxy optionally substituted with one, two or three substituents selected from the group consisting of amino, isocyanato (--N.dbd.C.dbd.O), isothiocyanato (--N.dbd.C.dbd.S), --NH--C(.dbd.O)--X or --NH--C(.dbd.S)--X;R.sup.8 is alkyl (C.sub.1 -C.sub.20), --(CH.sub.2).sub.m --Ar, or polyhydroxyalkyl (C.sub.1 -C.sub.Type: GrantFiled: April 13, 1994Date of Patent: December 19, 1995Assignee: Sterling Winthrop Inc.Inventors: Carl R. Illig, Thomas J. Caulfield, John L. Toner, Peng Guo, David L. Ladd
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Patent number: 5475013Abstract: Urea-containing hydroxyethylamine peptide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.Type: GrantFiled: May 20, 1992Date of Patent: December 12, 1995Assignee: Monsanto CompanyInventors: John J. Talley, Daniel P. Getman, John N. Freskos, Ko-Chung Lin, Robert M. Heintz, Donald J. Rogier, Jr., Deborah E. Bertenshaw
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Patent number: 5468775Abstract: The present invention concerns enaminones having the formula: ##STR1## wherein R is from the group consisting of COOCH.sub.3 and COOC.sub.2 H.sub.5 ; R.sup.1 is from the group consisting of H and CH.sub.3 ; R.sup.2 is from the group consisting of H when R.sup.1 is CH.sub.3 and CH.sub.3 when R.sup.1 is H; and R.sup.3 is from the group of first radicals consisting of benzyl, phenethyl, disubstituted phenyl and trisubstituted phenyl. The substituted species are second radicals having positive lipophilicity selected from the group consisting of F, Cl, Br, and I.Type: GrantFiled: March 2, 1993Date of Patent: November 21, 1995Assignee: Howard UniversityInventors: Kenneth R. Scott, Jesse M. Nicholson, Ivan O. Edafiogho
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Patent number: 5453468Abstract: The invention relates to two classes of prepolymers containing a perfluoropolyethereal chain and carboxylic end groups, suitable as cross-linking agents for epoxy prepolymers. The first class contains anhydride-derived end groups; the second lactone-derived end groups; prepolymers therefrom are also disclosed. Additional non-fluorinated curing agents may also be added.Type: GrantFiled: January 24, 1995Date of Patent: September 26, 1995Assignee: Ausimont S.p.A.Inventors: Leno Mascia, Claudio Tonelli, Giovanni Simeone
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Patent number: 5446192Abstract: .beta.-Aminoacrylic acid esters can be prepared by reacting acetic acid esters of the formulaH.sub.2 CR.sub.1 --COOR.sup.2 (II)with aminal esters of the formula ##STR1## at 0.5-10 bar and 50.degree.-170.degree. C. in an aprotic polar solvent. The radicals R.sup.1 to R.sup.7 are as defined in the description.Type: GrantFiled: March 3, 1993Date of Patent: August 29, 1995Assignee: Bayer AktiengesellschaftInventors: Helmut Kraus, Heinz-Ulrich Blank, Gerhard Marzolph
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Patent number: 5442105Abstract: A process for for producing a (2R,3S)-cyclohexylnorstatine or a salt thereof is disclosed, which comprises the steps of: enantioselectively hydrogenating a 4-cyclohexyl-2-halogeno-3-oxobutyric acid ester in the presence of a ruthenium-phosphine complex to produce a 4-cyclohexyl-2-halogeno-(3R)-hydroxybutyric acid ester (2); epoxidizing the compound (2) in the presence of a base to produce a 4-cyclohexyl-(2S,3R)-epoxybutyric acid ester (3); reacting the compound (3) with a lower trialkylsilyl azide in the presence of a Lewis acid to produce a (3S)-azide-4-cyclohexyl-(2S)-substituted butyric acid ester (4); subjecting the compound (4) to hydrogenolysis to produce a (2S,3S)-cyclohexylnorstatine derivative (5); and inverting the configuration at the 2-position of the compound (5).Type: GrantFiled: December 30, 1993Date of Patent: August 15, 1995Assignee: Takasago International CorporationInventors: Noboru Sayo, Noboru Sano, Hidenori Kumobayashi
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Patent number: 5428073Abstract: There are described new 2-cyclohexan-1-yl-amine derivatives of formula (I) ##STR1## in which A, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meaning given in the description, and processes for their preparation.The compounds of the formula (I) are used as anti-microbial agents.Type: GrantFiled: October 5, 1992Date of Patent: June 27, 1995Assignee: Bayer AktiengesellschaftInventors: Franz Kunisch, Peter Babczinski, Dieter Arlt, Wilhelm Brandes, Heinz-Wilhelm Dehne, Stefan Dutzmann, Manfred Plempel
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Patent number: 5424438Abstract: Polishes for metal surfaces, based on dispersions of waxes, fluorinated polymers and perfluoropolyoxyalkylene oils acquire high gloss characteristics combined with improved water-repellency and resistance to soiling of 0.1-5% by weight of at least a cationic emulsifier comprised in the general formula(I) R-L-Q.sup.+ X.sup.-where:R=a chain of perfluoropolyoxyalkylene units;L=a divalent organic group;Q=a polar group;X=a halogen, or a group of formulaCH.sub.3 -Phenylene-SO.sub.3.sup.-R"SO.sub.3.sup.-R"=F-(CF.sub.2).sub.m -;t=1 or 2;m=1-4.The polished containing the emulsifiers of formula (I) as well as the compounds comprised in said formula are claimed as new products.Type: GrantFiled: January 6, 1994Date of Patent: June 13, 1995Assignee: Ausimont S.p.A.Inventors: Alba Chittofrati, Viviana Boselli, Giovanni Gavazzi, Ezio Strepparola, Renato Spiti, Silvia Tresoldi
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Patent number: 5416117Abstract: A novel cyclopropenone derivative (I) which possesses a potent inhibitory activity against thiol protease such as papain, cathepsin B, cathepsin H, cathepsin L, calpain or the like with excellent properties regarding oral absorbance, tissue transference and cell membrane permeability, and are clinically useful in the treatment of various diseases such as muscular dystrophy, amyotrophy. Also provided are a process for producing the compound (I) and a pharmaceutical composition containing the same.Type: GrantFiled: February 28, 1994Date of Patent: May 16, 1995Assignee: Mitsubishi Kasei CorporationInventors: Ryoichi Ando, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
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Patent number: 5414017Abstract: Compounds of the formula ##STR1## wherein m is zero or 1; n is zero, 1 or 2; p is zero or 1 to 6 provided that m and p are not both zero; R.sub.3 is hydrogen, acyl, or benzyl; and R.sub.1 is hydrogen, alkyl, phenyl, substituted phenyl, phenyl-alkylene, heterocyclic-alkylene, etc. These compounds are useful as cardiovascular agents.Type: GrantFiled: March 26, 1993Date of Patent: May 9, 1995Assignee: E. R. Squibb & Sons, Inc.Inventors: Norma G. Delaney, George C. Rovnyak, Melanie J. Loots
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Patent number: 5354901Abstract: Perfluoro(cycloaliphatic methyleneoxyalkylene) compositions are provided. These compositions comprise perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds having (a) a perfluorocycloaliphatic moiety which can have up to two perfluoroalkyl substituents and a perfluoroalkylene substituent, and (b) a perfluoromethyleneoxyalkylene carbonyl fluoride radical, the methylene group of the radical being bonded to a ring carbon atom or the perfluoroalkylene substituent of the moiety and the alkylene group of the perfluoromethyleneoxyalkylene carbonyl fluoride being a perfluoro(methyl)methylene group, a perfluoroisopropyleneoxy(methyl)methylene group, or a poly(perfluoroisopropyleneoxy)perfluoro(methyl)methylene group having up to about 10 perfluoroisopropyleneoxy units.Type: GrantFiled: February 1, 1993Date of Patent: October 11, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard M. Flynn, Patricia M. Savu
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Patent number: 5347042Abstract: The invention relates to new optically active sulphur-containing amino acid derivatives, a process for their preparation, their polymerisation to give optically active polymers and the use of these optically active polymers as adsorbents for chromatographic separation of racemates into enantiomers.Type: GrantFiled: June 11, 1992Date of Patent: September 13, 1994Assignee: Bayer AktiengesellschaftInventors: Michael Grosse-Bley, Bruno Bomer, Rolf Grosser, Dieter Arlt, Walter Lange
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Patent number: 5336484Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and an x-ray producing agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract wherein ##STR2## Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy,n is 1-5;y is 0-4; andw is 1-4.Type: GrantFiled: March 31, 1993Date of Patent: August 9, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
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Patent number: 5328909Abstract: A novel cyclopropenone derivative (I) which possesses a potent inhibitory activity against thiol protease such as papain, cathepsin B, cathepsin H, cathepsin L, calpain or the like with excellent properties regarding oral absorbance, tissue transference and cell membrane permeability, and are clinically useful in the treatment of various diseases such as muscular dystrophy, amyotrophy. Also provided are a process for producing the compound (I) and a pharmaceutical composition containing the same.Type: GrantFiled: June 25, 1992Date of Patent: July 12, 1994Assignee: Mitsubishi Kasei CorporationInventors: Ryoichi Ando, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
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Patent number: 5329042Abstract: Provided is a novel (1R, 2S)-1-acyl-2-carboxycyclohex-4-ene derivative represented by the following general formula [I], and its producing method, ##STR1## (where R.sup.1 represents a hydrogen atom, a lower alkyl group, or substituted or unsubstituted aryl group, and R.sup.2 represents a hydrogen atom, or a lower alkyl group). Also provided is a method of producing a (3S, 4R)-4-substituted-3-carboxycyclopentanone derivative represented by the following general formula [A], ##STR2## (where R.sup.1 and R.sup.2 are the same as those mentioned above).Type: GrantFiled: December 24, 1992Date of Patent: July 12, 1994Assignee: Japan Tobacco Inc.Inventors: Junichi Haruta, Kazuhiko Sakuma, Akihiro Yasuda, Katsuyoshi Hara, Itsuo Uchida
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Patent number: 5318769Abstract: Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract whereinX= ##STR2## Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl, or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene, lower-alkoxy-carbonyloxy;n=1-5;y=0-4; andw=1-4in an aqueous pharmaceutically acceptable carrier.Type: GrantFiled: March 31, 1993Date of Patent: June 7, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
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Patent number: 5312962Abstract: The invention relates to a process for the production of organic compounds containing aldimine or ketimine groups by the reaction of compounds containing .beta.-ketoester groups with bis-aldimines or bis-ketimines with elimination of aldehyde or ketone and to the preferred compounds obtained by this process.Type: GrantFiled: July 2, 1992Date of Patent: May 17, 1994Assignee: Bayer AktiengesellschaftInventors: Walter Schafer, Hanns-Peter Muller
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Patent number: 5294733Abstract: Preparation of cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketene type compound of the formula (R.sub.1) (R.sub.2) C.dbd.C.dbd.O to give a polymer: ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1) (R.sub.2)--COOR.sub.3, the acids in the mixture are converted for esters. The hydroxy ester of the ester mixture is converted to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the product ##STR4## wherein: R is selected, e.g.Type: GrantFiled: May 20, 1993Date of Patent: March 15, 1994Assignee: Eastman Kodak CompanyInventor: Charles A. McCombs
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Patent number: 5294616Abstract: A series of non-peptide derivatives that are antagonists of the fibrinogen IIb/IIIa receptor and thus are platelet aggregation compounds useful in the prevention and treatment of diseases caused by thrombus formation.Type: GrantFiled: March 25, 1992Date of Patent: March 15, 1994Assignee: Merck & Co., Inc.Inventors: Mark E. Duggan, Melissa S. Egbertson, Wasyl Halczenko, George D. Hartman, Laura M. Turchi, William L. Laswell
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Patent number: 5286746Abstract: Antihypercholesterolemic activity is exhibited by compounds of the formula ##STR1## wherein: X is hydrogen, alkali metal or ammonium;Y is hydrogen, alkyl, cycloalkyl, aryl, or aralkyl; ##STR2## R is hydrogen, alkyl, ammonium, alkylammonium, or alkali metal (such as Na, Li, or K); andn is 1 or 2.Type: GrantFiled: December 20, 1991Date of Patent: February 15, 1994Assignee: E. R. Squibb & Sons, Inc.Inventor: Kathleen M. Poss
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Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace
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Patent number: 5268489Abstract: Unsaturated cycloaliphatic esters like higher hydrocarbyl, functionally substituted or polyunsaturated cyclohex-3-ene carboxylates, made directly by cycloaddition of dienes with dienophillic (meth/eth)acrylates, and their derivatives like epoxides and urethanes, provide useful thermal and radiation curable coatings, inks, sealants, adhesives, solvents, acid scavengers, and intermediates for other uses.Type: GrantFiled: February 5, 1993Date of Patent: December 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
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Patent number: 5264455Abstract: X is hydrogen or --S(O).sub.m --R.sup.1 and Y is hydrogen or S(O).sub.n --R.sup.2, except that X and Y are not both hydrogen, or one of X and Y is --S--alkyl--SH and the other is hydrogen; ##STR2## and the remaining symbols are as defined in the specification.Type: GrantFiled: July 1, 1991Date of Patent: November 23, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: Ravi K. Varma, Jeffrey O. Saunders, Sam T. Chao, Eric M. Gordon, Dinos P. Santafianos
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Patent number: 5264606Abstract: A process for the preparation of monomeric polyvinyl compounds and/or oligomers thereof comprising:(i) preactivating a supported rhenium oxide catalyst with a hydrocarbyl metal compound; and(ii) reacting, under metathesis reaction conditions, norbornene or one or more substituted norbornenes, or mixtures thereof, with ethylene in the presence of the activated supported catalyst of step (i).Type: GrantFiled: November 9, 1992Date of Patent: November 23, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Kenneth G. Moloy, Bernard D. Dombek
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Poly(aminoalkyl)aminocarbonyl aminoacyl aminodiol amino acid derivatives as anti-hypertensive agents
Patent number: 5246959Abstract: Non-peptidyl compounds characterized generally as poly(aminoalkyl)aminocarbonyl aminoacyl aminodiol derivatives of amino acids are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein X is selected from oxygen atom and methylene; wherein each of R.sub.9 and R.sub.10 is independently selected from hydrido, ethyl and methyl; wherein R.sub.9 and R.sub.10 may be taken together to form a heterocyclic ring having five or six ring atoms and containing one or two nitrogen atoms as ring atoms; wherein each of R.sub.1 and R.sub.2 is independently selected from hydrido, methyl, ethyl and isopropyl; wherein R.sub.3 is selected from benzyl, phenethyl, pyridylmethyl and 2-pyridylethyl; wherein each of R.sub.4 and R.sub.6 is hydrido; wherein R.sub.7 is cyclohexylmethyl; wherein R.sub.8 is selected from ##STR2## with the carbon bearing the hydroxyl radical being in the S configuration; wherein R.sub.Type: GrantFiled: December 16, 1991Date of Patent: September 21, 1993Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran -
Patent number: 5247125Abstract: Novel thiol-terminated hydroxyamides, and processes for their preparation and use are provided. These hydroxyamide compounds may be prepared by the reaction of a mercapto-functional alkyl ester, such as methylmercaptopropionate, with a molar excess of an alcohol-substituted amine, such as a b-hydroxyalkyl amine. The thiol-terminated hydroxyamides are useful as polymerization chain transfer agents, particularly when it is desirable to form polymers or oligomers containing functional hydroxyamide end groups. By chain terminating such polymers or oligomers with reactive hydroxyamide end groups the polymers or oligomers can be further reacted with acid-containing monomers or polymers to form block or graft copolymers.Type: GrantFiled: February 28, 1991Date of Patent: September 21, 1993Assignee: Rohm and Haas CompanyInventors: Andrew W. Gross, William D. Emmons
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Patent number: 5245060Abstract: A terpene derivative represented by the general formula (I): ##STR1## wherein R.sup.1 represents a lower alkyl group; R.sup.2 represents an alkyl group, a cycloalkyl group, a cycloalkylalkyl group, an aryl group, an arylalkyl group or a heteroaryl group; n is 0 or 1 or 2; and the symbol " " represents a single or double bond with the proviso that both of the linkages adjacent to each other are not simultaneously single bonds or double bonds which are useful for the preparation of drug, food, perfume and so on, and a process for preparing thereof.Type: GrantFiled: March 12, 1992Date of Patent: September 14, 1993Assignee: Eisai Co. Ltd.Inventors: Kimio Hamamura, Yoshio Urawa, Yukio Narabe, Yoshihiko Hisatake, Shizumasa Kijima
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Patent number: 5235101Abstract: An improved process for the separation of enantiomers of a mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding an inert liquid to the reaction solution formed by: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with less that equimolar equivalents of a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt; (iv) addition of a countersolvent to the slurry formed in step (iii); (v) extracting the more soluble diastereomeric salt or the salt of carboxylic acid and the base added in step (i) into the countersolvent. The inert liquid and the countersolvent must be of sufficiently different density.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
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Patent number: 5235100Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises:i) separating a racemic mixture of an aliphatic carboxylic acid or ester thereof having the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; cycloalkyl; alkyl-substituted cycloalkyl; C.sub.6 to C.sub.14 aryl; C.sub.1 to C.sub.6 alkylthio; C.sub.2 to C.sub.8 cycloalkylthio; C.sub.6 to C.sub.10 arylthio; C.sub.6 to C.sub.10 arylcarbonyl; C.sub.4 to C.sub.8 cycloalkenyl; trifluoromethyl; halo; or C.sub.4 to C.sub.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
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Patent number: 5235095Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base; and (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt, the improvement being adding to the salt solution of step (ii) an inert organic or inorganic base that is soluble in the salt solution.Type: GrantFiled: January 24, 1992Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventors: Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
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Patent number: RE34652Abstract: Novel fluorinated, acrylamide monomers are prepared from 2-alkenyl azlactones reacted with fluorinated alcohols. The novel monomers have the formula ##STR1## wherein R.sup.1 and R.sup.6 are independently hydrogen or methyl;R.sup.2 and R.sup.3 independently can be an alkyl, cycloalkyl, or aryl group, or R.sup.2 and R.sup.3 taken together with the carbon to which they are joined can form a carbocyclic ring containing 4 to 12 ring atoms;R.sup.4 and R.sup.5 are independently hydrogen or lower alkyl;a is 0 or 1;b is 1 or 2;X is a single bond, CH.sub.2, CH.sub.2 OCH.sub.2, and CH.sub.2 CH.sub.2 OCH.sub.2 ; andR.sub.F is a substantially perfluorinated alkyl, cycloalkyl, or aryl group when b is 1 and perfluorinated alkylene when b is 2.Novel polymers and copolymers can be prepared from the monomers of the invention.Type: GrantFiled: June 3, 1992Date of Patent: June 28, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Steven M. Heilmann, Larry R. Krepski, Dean M. Moren, Jerald K. Rasmussen, Howell K. Smith, II