Alicyclic Acid Moiety Containing N, S, P, B Or Halogen Patents (Class 560/125)
  • Patent number: 5614522
    Abstract: Urea-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
    Type: Grant
    Filed: July 24, 1995
    Date of Patent: March 25, 1997
    Assignee: G.D. Searle & Co.
    Inventors: John J. Talley, Kathryn L. Reed
  • Patent number: 5610297
    Abstract: 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: Grant
    Filed: October 6, 1995
    Date of Patent: March 11, 1997
    Assignee: Georgia Tech Research Corp.
    Inventor: James C. Powers
  • Patent number: 5602196
    Abstract: 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: Grant
    Filed: November 27, 1995
    Date of Patent: February 11, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Bernard Gilg, Rita Pitteloud
  • Patent number: 5597938
    Abstract: 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: Grant
    Filed: August 10, 1995
    Date of Patent: January 28, 1997
    Assignees: Taisho Pharmaceutical Co., Ltd., Fumie Sato
    Inventor: Fumie Sato
  • Patent number: 5587514
    Abstract: 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: Grant
    Filed: November 8, 1993
    Date of Patent: December 24, 1996
    Assignee: Emory University
    Inventors: Dennis C. Liotta, Bharat R. Lagu
  • Patent number: 5583248
    Abstract: 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: Grant
    Filed: April 5, 1995
    Date of Patent: December 10, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Joseph A. Martin, Gareth J. Thomas
  • Patent number: 5569778
    Abstract: 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: Grant
    Filed: April 28, 1995
    Date of Patent: October 29, 1996
    Assignee: Daikin Industries Ltd.
    Inventors: Teruo Umemoto, Ginjiro Tomizawa
  • Patent number: 5561211
    Abstract: 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: Grant
    Filed: May 23, 1995
    Date of Patent: October 1, 1996
    Assignee: Bayer Corporation
    Inventors: Kenneth P. Yonek, Lyuba K. Gindin, Douglas A. Wicks
  • Patent number: 5536723
    Abstract: 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: Grant
    Filed: October 6, 1994
    Date of Patent: July 16, 1996
    Assignee: Brigham & Women's Hospital
    Inventors: Joseph Loscalzo, John Cooke
  • Patent number: 5523462
    Abstract: Cyclohexenone derivatives I ##STR1## The cyclohexenone derivatives I are suitable as herbicides and for regulating plant growth.
    Type: Grant
    Filed: April 19, 1994
    Date of Patent: June 4, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Kast, Thomas Zierke, Matthias Bratz, Ulf Misslitz, Norbert Meyer, Andreas Landes, Wilhelm Rademacher, Karl-Otto Westphalen, Helmut Walter
  • Patent number: 5502221
    Abstract: 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: Grant
    Filed: May 5, 1995
    Date of Patent: March 26, 1996
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Noboru Sano, Hidenori Kumobayashi
  • Patent number: 5491145
    Abstract: 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: Grant
    Filed: November 21, 1994
    Date of Patent: February 13, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
  • Patent number: 5491169
    Abstract: 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: Grant
    Filed: September 26, 1994
    Date of Patent: February 13, 1996
    Assignee: Institut National de la Sante et de la Recherche Medicale (INSERM)
    Inventors: Bernard Roques, Marie C. Fournie-Zaluski
  • Patent number: 5491170
    Abstract: .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: Grant
    Filed: December 19, 1994
    Date of Patent: February 13, 1996
    Assignee: Warner-Lambert Company
    Inventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
  • Patent number: 5489704
    Abstract: 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: Grant
    Filed: August 29, 1994
    Date of Patent: February 6, 1996
    Assignees: Bayer Corporation, Bayer Aktiengesellschaft
    Inventors: Edward P. Squiller, Christian Zweiner
  • Patent number: 5482947
    Abstract: Urea-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
    Type: Grant
    Filed: November 15, 1993
    Date of Patent: January 9, 1996
    Inventors: 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
  • Patent number: 5481026
    Abstract: 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: Grant
    Filed: July 1, 1994
    Date of Patent: January 2, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Grosse-Bley, Bruno Bomer, Rolf Grosser, Walter Lange, Franz-Peter Hoever, Dieter Arlt
  • Patent number: 5481034
    Abstract: 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: Grant
    Filed: November 29, 1994
    Date of Patent: January 2, 1996
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Bum-Tae Kim, Yong-Ki Min, No-Kyun Park, Tae-Jun Kim, Kwang-Yun Cho
  • Patent number: 5476966
    Abstract: 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: Grant
    Filed: January 13, 1995
    Date of Patent: December 19, 1995
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Mary Anderson, Alton Meister
  • Patent number: 5476644
    Abstract: 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: Grant
    Filed: April 13, 1994
    Date of Patent: December 19, 1995
    Assignee: Sterling Winthrop Inc.
    Inventors: Carl R. Illig, Thomas J. Caulfield, John L. Toner, Peng Guo, David L. Ladd
  • Patent number: 5475013
    Abstract: Urea-containing hydroxyethylamine peptide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
    Type: Grant
    Filed: May 20, 1992
    Date of Patent: December 12, 1995
    Assignee: Monsanto Company
    Inventors: John J. Talley, Daniel P. Getman, John N. Freskos, Ko-Chung Lin, Robert M. Heintz, Donald J. Rogier, Jr., Deborah E. Bertenshaw
  • Patent number: 5468775
    Abstract: 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: Grant
    Filed: March 2, 1993
    Date of Patent: November 21, 1995
    Assignee: Howard University
    Inventors: Kenneth R. Scott, Jesse M. Nicholson, Ivan O. Edafiogho
  • Patent number: 5453468
    Abstract: 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: Grant
    Filed: January 24, 1995
    Date of Patent: September 26, 1995
    Assignee: Ausimont S.p.A.
    Inventors: Leno Mascia, Claudio Tonelli, Giovanni Simeone
  • Patent number: 5446192
    Abstract: .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: Grant
    Filed: March 3, 1993
    Date of Patent: August 29, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Kraus, Heinz-Ulrich Blank, Gerhard Marzolph
  • Patent number: 5442105
    Abstract: 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: Grant
    Filed: December 30, 1993
    Date of Patent: August 15, 1995
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Noboru Sano, Hidenori Kumobayashi
  • Patent number: 5428073
    Abstract: 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: Grant
    Filed: October 5, 1992
    Date of Patent: June 27, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz Kunisch, Peter Babczinski, Dieter Arlt, Wilhelm Brandes, Heinz-Wilhelm Dehne, Stefan Dutzmann, Manfred Plempel
  • Patent number: 5424438
    Abstract: 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: Grant
    Filed: January 6, 1994
    Date of Patent: June 13, 1995
    Assignee: Ausimont S.p.A.
    Inventors: Alba Chittofrati, Viviana Boselli, Giovanni Gavazzi, Ezio Strepparola, Renato Spiti, Silvia Tresoldi
  • Patent number: 5416117
    Abstract: 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: Grant
    Filed: February 28, 1994
    Date of Patent: May 16, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
  • Patent number: 5414017
    Abstract: 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: Grant
    Filed: March 26, 1993
    Date of Patent: May 9, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Norma G. Delaney, George C. Rovnyak, Melanie J. Loots
  • Patent number: 5354901
    Abstract: 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: Grant
    Filed: February 1, 1993
    Date of Patent: October 11, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Richard M. Flynn, Patricia M. Savu
  • Patent number: 5347042
    Abstract: 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: Grant
    Filed: June 11, 1992
    Date of Patent: September 13, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Grosse-Bley, Bruno Bomer, Rolf Grosser, Dieter Arlt, Walter Lange
  • Patent number: 5336484
    Abstract: 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: Grant
    Filed: March 31, 1993
    Date of Patent: August 9, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
  • Patent number: 5328909
    Abstract: 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: Grant
    Filed: June 25, 1992
    Date of Patent: July 12, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
  • Patent number: 5329042
    Abstract: 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: Grant
    Filed: December 24, 1992
    Date of Patent: July 12, 1994
    Assignee: Japan Tobacco Inc.
    Inventors: Junichi Haruta, Kazuhiko Sakuma, Akihiro Yasuda, Katsuyoshi Hara, Itsuo Uchida
  • Patent number: 5318769
    Abstract: 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: Grant
    Filed: March 31, 1993
    Date of Patent: June 7, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
  • Patent number: 5312962
    Abstract: 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: Grant
    Filed: July 2, 1992
    Date of Patent: May 17, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Schafer, Hanns-Peter Muller
  • Patent number: 5294733
    Abstract: 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: Grant
    Filed: May 20, 1993
    Date of Patent: March 15, 1994
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • Patent number: 5294616
    Abstract: 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: Grant
    Filed: March 25, 1992
    Date of Patent: March 15, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Mark E. Duggan, Melissa S. Egbertson, Wasyl Halczenko, George D. Hartman, Laura M. Turchi, William L. Laswell
  • Patent number: 5286746
    Abstract: 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: Grant
    Filed: December 20, 1991
    Date of Patent: February 15, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Kathleen M. Poss
  • Patent number: 5278338
    Abstract: 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: Grant
    Filed: November 4, 1992
    Date of Patent: January 11, 1994
    Assignee: Ethyl Corporation
    Inventor: Rhonda L. Trace
  • Patent number: 5268489
    Abstract: 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: Grant
    Filed: February 5, 1993
    Date of Patent: December 7, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
  • Patent number: 5264455
    Abstract: 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: Grant
    Filed: July 1, 1991
    Date of Patent: November 23, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Ravi K. Varma, Jeffrey O. Saunders, Sam T. Chao, Eric M. Gordon, Dinos P. Santafianos
  • Patent number: 5264606
    Abstract: 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: Grant
    Filed: November 9, 1992
    Date of Patent: November 23, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Kenneth G. Moloy, Bernard D. Dombek
  • Patent number: 5246959
    Abstract: 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: Grant
    Filed: December 16, 1991
    Date of Patent: September 21, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran
  • Patent number: 5247125
    Abstract: 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: Grant
    Filed: February 28, 1991
    Date of Patent: September 21, 1993
    Assignee: Rohm and Haas Company
    Inventors: Andrew W. Gross, William D. Emmons
  • Patent number: 5245060
    Abstract: 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: Grant
    Filed: March 12, 1992
    Date of Patent: September 14, 1993
    Assignee: Eisai Co. Ltd.
    Inventors: Kimio Hamamura, Yoshio Urawa, Yukio Narabe, Yoshihiko Hisatake, Shizumasa Kijima
  • Patent number: 5235101
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
  • Patent number: 5235100
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
  • Patent number: 5235095
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
  • Patent number: RE34652
    Abstract: 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: Grant
    Filed: June 3, 1992
    Date of Patent: June 28, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Steven M. Heilmann, Larry R. Krepski, Dean M. Moren, Jerald K. Rasmussen, Howell K. Smith, II