Amide In Acid Moiety Patents (Class 560/41)
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Patent number: 6037498Abstract: This invention relates to novel compounds of general formula (I) ##STR1## wherein R.sup.1 represents an organic group, R.sup.2 represents a hydrogen atom or an organic group, and the asterisk denotes that the group R.sup.1 is predominantly in the R- or S-configuration such that the compound is in substantially enantiomerically pure form. The compounds are a useful source of chiral nucleophiles, e.g. undergoing stereoselective Michael addition to .alpha.,.beta.-unsaturated carboxylic acid derivatives.Type: GrantFiled: August 12, 1996Date of Patent: March 14, 2000Assignee: Oxford Asymmetry International PLCInventors: Stephen Graham Davies, Mario Eugenio Cosamino Polywka, David Roy Fenwick, Frank Reed
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Patent number: 6031121Abstract: Optically active N-(S-2-acetylthiomethyl-1-oxo-3-phenylpropyl)-glycine benzyl ester useful as an enkephalin inhibitory agent or ACE inhibitory agent can be produced at low cost in an industrial manner, by a method comprising subjecting optically active 2-hydroxymethyl-3-phenylpropionic acid and glycine benzyl ester to condensation to subsequently convert the hydroxyl group into an elimination group, and substituting the elimination group with an acetylthio group.Type: GrantFiled: February 16, 1999Date of Patent: February 29, 2000Assignee: Ajinomoto Co., Inc.Inventors: Takayuki Suzuki, Takayuki Hamada, Kunisuke Izawa
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Patent number: 6017925Abstract: This invention relates to certain novel compounds and derivatives thereof, their synthesis, and their use as vitronectin receptor antagonists. The vitronectin receptor antagonist compounds of the present invention are .alpha.v.beta.3 antagonists, .alpha.v.beta.5 antagonists or dual .alpha.v.beta.3/.alpha.v.beta.5 antagonists useful for inhibiting bone resorption, treating and preventing osteoporosis, and inhibiting restenosis, diabetic retinopathy, macular degeneration, angiogenesis, atherosclerosis, inflammation, viral disease, and tumor growth.Type: GrantFiled: January 13, 1998Date of Patent: January 25, 2000Assignee: Merck & Co., Inc.Inventor: Mark E. Duggan
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Patent number: 6004992Abstract: The present invention relates to novel fluorobutenyl aminocarboxylates of the formula (I)R--CO--O--CH.sub.2 --CH.sub.2 --CX.dbd.CF.sub.2 (I)in whichX represents hydrogen or halogen andR represents one of the groups ##STR1## (b) R.sup.3 --A--CO--NR.sup.4 --CR.sup.5 R.sup.6 -- or ##STR2## in which A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each as defined in the description, to processes for their preparation and to their use for controlling animal pests.Type: GrantFiled: May 22, 1998Date of Patent: December 21, 1999Assignee: Bayer AktiengesellschaftInventors: Udo Kraatz, Wolfram Andersch, Andreas Turberg, Norbert Mencke
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Patent number: 5985922Abstract: Provided is a novel active oxygen-resisting agent which has an excellent active oxygen resistance and which exhibits a good solubility in an oil solvent. An active oxygen-resisting agent containing as an active ingredient an amino acid derivative represented by the following formula (I) ##STR1## wherein Ar represents a substituted or substituted 2-hydroxyphenyl group or a pyridyl group, said substitution being selected from the group consisting of a halogen atom, a C.sub.1-6 alkyl group, a hydroxyl group, a hydroxy C.sub.1-6 alkyl group, a nitro group, a C.sub.1-6 alkoxyl group or a carboxyl group, R.sup.1 represents a side chain of an amino acid, X represents --O-- or --NH--, R.sup.2 represents a C.sub.8-22 alkyl group, and n represents 0 or 1, or its salt.Type: GrantFiled: April 3, 1998Date of Patent: November 16, 1999Assignee: Ajinomoto Co., Inc.Inventors: Manabu Kitazawa, Kazutami Sakamoto, Keiji Iwasaki
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Patent number: 5986132Abstract: Compounds of formula (I) wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, X are as defined in the specification and are prepared by elimination of one of the groups X.sub.1 and X.sub.2 from a compound of formula (II) wherein X.sub.1 and X.sub.2 each independently represent a carboxylic acid group or salt thereof, or a protected carboxylic acid group, the non-eliminated group X.sub.1 or X.sub.2 corresponding to the group X in the desired compound of formula (I).Type: GrantFiled: May 14, 1998Date of Patent: November 16, 1999Assignee: British Biotech Pharmaceuticals Ltd.Inventors: Maxwell Reeve, Stephen Arthur Bowles
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Patent number: 5985911Abstract: C-terminal compounds of formula ##STR1## are potent inhibitors of matrix metalloproteinase and are useful in the treatment of diseases in which matrix metalloproteinase play a role. Also disclosed are matrix metalloproteinase inhibiting compositions and a method of inhibiting matrix metalloproteinase in a mammal.Type: GrantFiled: December 17, 1997Date of Patent: November 16, 1999Assignee: Abbott LaboratoriesInventors: Steven K. Davidsen, Alan S. Florjancic, George S. Sheppard, Jamie R. Giesler, Lianhong Xu, Yan Guo, Michael L. Curtin, Michael R. Michaelides, Carol K. Wada, James H. Holms
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Patent number: 5981573Abstract: A compound represented by general formula (I) or a pharmaceutically acceptable salt or ester thereof: [wherein each of Ar.sup.1, Ar.sup.2, Ar.sup.3 and Ar.sup.4 is an aryl group or an aromatic heterocyclic group; A.sup.1 is a C.sub.2-6 chain hydrocarbon group or a group represented by --A.sup.1a --W.sup.1 --A.sup.1b -- (wherein W.sup.1 is an oxygen atom, a sulfur atom, an ethynylene group, a cyclopropylene group or a group represented by --NR.sup.W --; A.sup.2 is a C.sub.2-8 chain hydrocarbon group; each of X and Y is an oxygen atom, a sulfur atom, a carbonyl group or a group represented by --CHR.sup.a -- or by --NR.sup.b --, or X and Y together represent a vinylene group or an ethynylene group; each of R.sup.1, R.sup.2, R.sup.3, R.sup.7 and R.sup.8 is a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group, a lower alkenyl group or a lower alkoxy group; each of R.sup.4 and R.sup.Type: GrantFiled: August 4, 1998Date of Patent: November 9, 1999Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Yoshikazu Iwasawa, Tetsuya Aoyama, Kumiko Kawakami, Sachie Arai, Toshihiko Satoh, Yoshiaki Monden
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Patent number: 5981556Abstract: 1,3-diazolino and 1,3-diazolidino heterocycle derivatives useful as nitric oxide synthase inhibitors.Type: GrantFiled: July 22, 1997Date of Patent: November 9, 1999Assignee: G.D. Searle & Co.Inventors: Donald W. Hansen, Jr., Arija A. Bergmanis, Timothy J. Hagen, E. Ann Hallinan, Steven W. Kramer, Suzanne Metz, Karen B. Peterson, Barnett S. Pitzele, Foe S. Tjoeng, Mihaly V. Toth, Mahima Trivedi, R. Keith Webber, Sofya Tsymbalov, Rolando E. Gapud
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Patent number: 5952386Abstract: The present invention provides dihalopropene compounds of the general formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl or the like; L is C(.dbd.O)NH or the like; R.sub.2, R.sub.3 and R.sub.4 are independently halogen or the like; R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen or the like; m is an integer of 0 to 4; n is an integer of 0 to 2; X is chlorine or the like; Y is oxygen or the like; and Z is oxygen or the like, which have excellent insecticidal activity so that they are satisfactorily effective for the control of noxious insects.Type: GrantFiled: September 24, 1997Date of Patent: September 14, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Sanshiro Matsuo, Taro Hirose, Keiichi Izumi, Masaya Suzuki, Noriyasu Sakamoto, Kazunori Tsushima, Shigeru Saito, Hirotaka Takano
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Patent number: 5902737Abstract: A process for the preparation of disodium Z-L-aspartate from fumaric acid, in whicha) fumaric acid is reacted with ammonia in an inert diluent in the presence of aspartase or aspartase-producing microorganisms to give ammonium L-aspartate thenb) the ammonium L-aspartate-containing solution is treated with sodium hydroxide, forming, depending on the amount of sodium hydroxide used, the mono- or disodium L-aspartate or a mixture thereof, andc) the eliminated ammonia is returned to a fumaric acid suspension, which is used as starting solution for further enzymatic reactions, and thend) the residual mono and/or disodium L-aspartate-containing solution is reacted with benzyloxycarbonyl chloride at a pH of between 9 and 14, with the simultaneous addition of sodium hydroxide, to form disodium Z-L-aspartate.Type: GrantFiled: September 19, 1997Date of Patent: May 11, 1999Assignees: DSM Fine Chemicals Austria GmbH, Holland Sweetener Company V.o.V.Inventors: Gerald Kirchner, Erik Salzbrenner, Christian Werenka, Wilhelmus Boesten
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Patent number: 5888972Abstract: A compound of the formula: ##STR1## in which R.sup.4 is acyl,R.sup.5 is lower alkyl,R.sup.6 is optionally substituted ar(lower)alkyl or optionally substituted heterocyclic-(lower)alkyl,R.sup.7 is lower alkyl or lower alkylthio(lower)alkyl,R.sup.8 is carboxy or protected carboxy,A is lower alkylene,Z is a group of the formula: ##STR2## wherein R.sup.1 is hydrogen, lower alkyl, common amino-protective group or optionally substituted ar(lower)alkyl,R.sup.2 is hydrogen, lower alkyl, optionally substituted ar(lower)alkyl, optionally substituted heterocyclic-(lower)alkyl, optionally substituted cyclo(lower)alkyl(lower)alkyl, common amino-protective group, amino(or protected amino)(lower)alkyl, optionally substituted heterocyclic-carbonyl or cyclo(lower)alkyl, andR.sup.3 is optionally substituted heterocyclic(lower)alkyl, andm is an integer of 0 to 2,or pharmaceutically acceptable salts thereof, useful as endothelin antagonist.Type: GrantFiled: June 24, 1997Date of Patent: March 30, 1999Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Keiji Hemmi, deceased, Masahiro Neya, Naoki Fukami, Natsuko Kayakiri, Hirokazu Tanaka
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Patent number: 5874609Abstract: A crystalline L-alpha-aspartyl-L-phenyl-alanine methyl ester product is disclosed. The product is obtained by crystallizing the ester from an aqueous solution, by cooling. The initial concentration of ester in the aqueous solution used provides at least 10 grams of precipitated solid phase per liter of solution. The solution is cooled through conductive heat transfer without effecting forced flow to form a sherbet-like pseudo solid phase.Type: GrantFiled: August 26, 1997Date of Patent: February 23, 1999Assignee: Ajinomoto Company IncorporatedInventors: Masayoshi Naruse, Haruo Kawasaki, Shinichi Kishimoto, Harutoshi Oura, Masao Nakamura, Hideo Takeda
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Patent number: 5859282Abstract: A method for dissolving crystalline L-alpha-aspartyl-L-phenyl alanine methyl ester product is disclosed. The product is obtained by crystallizing the ester from an aqueous solution, by cooling. The initial concentration of ester in the aqueous solution used provides at least 10 grams of precipitated solid phase per liter of solution.Type: GrantFiled: May 31, 1996Date of Patent: January 12, 1999Assignee: Ajinomoto Company IncorporatedInventors: Masayoshi Naruse, Haruo Kawasaki, Shinichi Kishimoto, Harutoshi Oura, Masao Nakamura, Hideo Takeda
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Patent number: 5859047Abstract: Inhibitors for matrix metalloproteases, pharmaceutical compositions containing them, and a process for using them to treat a variety of physiological conditions. The compounds of the invention have the generalized formula ##STR1## wherein each T is a substituted group; x is 0, 1, or 2; the group D represents ##STR2## the group R6 represents a variety of possible substituent groups on the carbon chain between D and G, and the group G represents M, ##STR3## in which M represents --CO.sub.2 H, --CON(R.sup.11).sub.2, or --CO.sub.2 R.sup.12 ; and R.sup.13 represents any of the side chains of the 19 noncyclic naturally occurring amino acids.Type: GrantFiled: May 30, 1997Date of Patent: January 12, 1999Assignee: Bayer CorporationInventors: Harold Clinton Eugene Kluender, David Ross Brittelli, William Harrison Bullock, Kerry Jeanne Combs, Brian Richard Dixon, Michael Christopher VanZandt, Scott McClelland Wilhelm, Donald John Wolanin
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Patent number: 5856311Abstract: Compounds based on derivatives of .beta.-aminopropionic acid having the general formula (I): ##STR1## The compounds having general formula (I) have a high antifungal activity.Type: GrantFiled: October 23, 1995Date of Patent: January 5, 1999Assignee: Isagro Ricerca SrlInventors: Giovanni Camaggi, Lucio Filippini, Marilena Gusmeroli, Silvia Mormile, Ernesto Signorini, Carlo Garavaglia
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Patent number: 5856490Abstract: Compounds of the formula ##STR1## where the symbols have the meaning defined in the specification have retinoid-like biological activity.Type: GrantFiled: September 4, 1997Date of Patent: January 5, 1999Assignee: AllerganInventors: Min Teng, Tien T. Duong, Roshantha A. Chandraratna
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Patent number: 5847005Abstract: The present invention relates to benzamidoxime derivatives represented by the formula ?I!; ##STR1## wherein R.sup.1 is unsubstituted or substituted C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted C.sub.2 -C.sub.4 alkenyl or unsubstituted or substituted C.sub.2 -C.sub.4 alkynyl, R.sup.2 is phenyl optionally having substituents or heterocycle optionally having substituents, X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each independently hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio or the like, and r.sub.1 and r.sub.2 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl or the like, having excellent fungicidal activity and being useful as a fungicide for agricultural and horticultural use, and methods for preparation thereof.Type: GrantFiled: August 14, 1997Date of Patent: December 8, 1998Assignee: Nippon Soda Co., Ltd.Inventors: Isamu Kasahara, Hirohito Ooka, Shinsuke Sano, Hiroyasu Hosokawa, Homare Yamanaka
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Patent number: 5831115Abstract: The present invention provides a compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof, which are useful for inhibiting protein farnesyltransferase and the farnesylation of the oncogene protein Ras or inhibiting de novo squalene production resulting in the inhibition of cholesterol biosynthesis, processes for the preparation of the compounds of the invention in addition to intermediates useful in these processes, a pharmaceutical composition, and to methods of using such compounds.Type: GrantFiled: April 11, 1996Date of Patent: November 3, 1998Assignee: Abbott LaboratoriesInventors: David L Arendsen, William R. Baker, Stephen A Fakhoury, Anthony K. L. Fung, David S. Garvey, William J. McClellan, Stephen J. O'Connor, Rajnandan N. Prasad, Todd W. Rockway, Saul H. Rosenberg, Herman H. Stein, Wang Shen, David M. Stout, Gerard M. Sullivan, David J. Augeri
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Patent number: 5827562Abstract: The process of the present invention is conducted in a liquid medium and concerns the preparation of a sweetening salt as the reaction product from two sweetener components in which one component is a sweetener derived from aspartic acid and the other is an intense sweetener not derived from aspartic acid. The process steps include adding to a liquid medium, in any order, a sweetener derived from aspartic acid, a derivative, such as a salt, of a sweetening acid not derived from aspartic acid, and a strong acid whereby a liquid system is obtained, allowing the components then present in the liquid system to react for at least one minute such that the sweetening salt formed, and isolating the sweetening salt. Novel sweetening salts having a good thermal stability and a low moisture content, as well as a new crystal modification of the sweetening salt from aspartame and acesulfamic acid are also disclosed. The sweetening salts can be used in foodstuff and the like.Type: GrantFiled: October 10, 1996Date of Patent: October 27, 1998Assignee: Holland Sweetener Company V.o.F.Inventors: John C. Fry, Jacob Van Soolingen
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Patent number: 5817603Abstract: Substituted cyclohexene-1,2-dicarboxylic acid derivatives I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are herein defined, or the agriculturally useful salts of Ia and Ib and intermediates for their preparation, which compounds are useful as herbicides and for the desiccation/defoliation of plants.Type: GrantFiled: February 11, 1997Date of Patent: October 6, 1998Assignee: BASF AktiengesellschaftInventors: Ralf Klintz, Elisabeth Heistracher, Peter Schaefer, Gerhard Hamprecht, Peter Plath, Uwe Kardorff, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter
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Patent number: 5807807Abstract: Substituted phthalimidocinnamic acid derivatives I ##STR1## wherein the variables are as defined in the description are useful as herbicides and for the desiccation and/or defoliation of plants.Type: GrantFiled: September 12, 1997Date of Patent: September 15, 1998Assignee: BASF AktiengesellschaftInventors: Elisabeth Heistracher, Peter Plath, Christoph-Sweder von dem Bussche-Hunnefeld, Gerhard Hamprecht, Ralf Klintz, Peter Schafer, Karl-Otto Westphalen, Helmut Walter, Matthias Gerber, Ulf Misslitz
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Patent number: 5804595Abstract: The invention provides certain amino acid conjugates of substituted 2-phenyl-N-?1-(phenyl)-2-(1-heterocycloalkyl- or heterocycloaryl-)ethyl!acetamides useful for selectively agonizing kappa opioid receptors in mammalian tissue.Type: GrantFiled: December 5, 1995Date of Patent: September 8, 1998Assignee: Regents of the University of MinnesotaInventors: Philip S. Portoghese, An-Chih Chang
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Patent number: 5804581Abstract: Matrix metalloprotease inhibiting compounds, pharmaceutical compositions thereof and a method of disease treatment using such compounds are presented. The compounds of the invention have the generalized formula: ##STR1## wherein T is a substituent and R.sup.24 is a substituted amide moiety. These compounds are useful for inhibiting matrix metalloproteases and, therefore, combating conditions to which MMP's contribute, such as osteoarthritis, rheumatoid arthritis, septic arthritis, periodontal disease, corneal ulceration, proteinuria, aneurysmal aortic disease, dystrophobic epidermolysis, bullosa, conditions leading to inflammatory responses, osteopenias mediated by MMP activity, tempera mandibular joint disease, demyelating diseases of the nervous system, tumor metastasis or degenerative cartilage loss following traumatic joint injury, and coronary thrombosis from athrosclerotic plaque rupture. The present invention also provides pharmaceutical compositions and methods for treating such conditions.Type: GrantFiled: May 15, 1997Date of Patent: September 8, 1998Assignee: Bayer CorporationInventor: Donald J. Wolanin
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Patent number: 5801195Abstract: Novel aryl amides are inhibitors of tumor necrosis factor .alpha. and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is N-benzoyl-3-amino-3-(3',4'-dimethoxyphenyl)propanamide.Type: GrantFiled: December 30, 1994Date of Patent: September 1, 1998Assignee: Celgene CorporationInventors: George W. Muller, Mary Shire, David I. Stirling
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Patent number: 5783735Abstract: A process for preparing polymeric amides is disclosed. The process comprises sequentially reacting a hydrocarbon polymer functionalized (e.g., via the Koch reaction) to contain acid, ester, thioacid and/or thioester groups with a heavy polyamine to form a partially derivatized product in which at least about 85% of the functional groups are converted to heavy (thio)amide groups, and then reacting the partially derivatized product with an excess of light amine to complete the derivatization by converting substantially all of the remaining functional groups to light (thio)amide groups. Products of the foregoing process are also disclosed, which products are useful as additives in fuels and in lubricants.Type: GrantFiled: May 25, 1995Date of Patent: July 21, 1998Assignee: Exxon Chemical Patents Inc.Inventors: Jacob I. Emert, Joseph V. Cusumano, David C. Dankworth, William D. Diana, William B. Eckstrom, Keith R. Gorda, Antonio Gutierrez, Jon E. Stanat, Warren A. Thaler, Stephen Zushma
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Patent number: 5782938Abstract: This invention concerns a an amidoalkanolaminoester composition obtained by reacting: (1) a reaction product of dialkyl maleate such as diethyl maleate and an alkylalkanolamine such as N-methylethanolamine; with (2) a hydrocarbyl oxypolyoxyalkene amine represented by the formula ##STR1## in which R represents an alkyl, an alicyclic, an alkylalicyclic radical having from 12 to 30 carbon atoms, or R'--Ar--; wherein R' represents a hydrocarbyl radical having from 4 to 12 carbon atoms; wherein x has a value of from about 10 to 16; wherein Ar is a divalent aromatic moiety such as divalent benzene; and wherein R" is an ethyl or methyl radical or a mixture of methyl and ethyl radicals. The amidoalkanolaminoester may be used as a fuel additive.Type: GrantFiled: May 23, 1997Date of Patent: July 21, 1998Assignee: Huntsman Petrochemical CorporationInventor: Wei-Yang Su
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Patent number: 5744632Abstract: A crystalline L-.alpha.-aspartyl-L-phenylalanine methyl ester product and the process for obtaining the same are disclosed. This product is obtained by adjusting the initial concentration of L-.alpha.-aspartyl-L-phenylalanine methyl ester in an aqueous solution so that the amount of precipitated solid, formed after cooling said solution, is about 10 grams or more of precipitate per liter of solvent. The solution is then cooled through conductive heat transfer, without causing forced flow, to obtain a sherbet-like pseudo solid phase.Type: GrantFiled: May 31, 1995Date of Patent: April 28, 1998Assignee: Ajinomoto Company IncorporatedInventors: Masayoshi Naruse, Haruo Kawasaki, Shinichi Kishimoto, Harutoshi Oura, Masao Nakamura, Hideo Takeda
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Patent number: 5733883Abstract: Improved method for crystallization of .alpha.-L-aspartyl-L-phenylalanine methyl ester (aspartame) from an aqueous solution by conductive cooling while avoiding turbulence in the crystallizing system wherein crystallization is carried out with cooling to a temperature level not lower than 10.degree. C. in the presence of at least 0.1% by weight of a C.sub.3-8 ketone, the amount of ketone and the temperature level being chosen for each individual ketone so that a homogeneous solvent system is present at the start of crystallization and an open drainable network of aspartame crystals is obtained.Type: GrantFiled: June 28, 1996Date of Patent: March 31, 1998Assignee: Holland Sweetener Company V.O.F.Inventors: Marinus P. W. M. Rijkers, Alexander P. M. Vrinzen
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Patent number: 5728863Abstract: Wet crystals of .alpha.-L-aspartyl-L-phenylalanine methyl ester with low water content can be obtained with high efficiency by solid-liquid separation of an aqueous suspension of .alpha.-L-aspartyl-L-phenylalanine methyl ester. The aqueous suspension is compressed at a final pressure of at least 20 kg/cm.sup.2 as a bearing pressure, and the wet crystals are dried after compression.Type: GrantFiled: February 15, 1996Date of Patent: March 17, 1998Assignee: Ajinomoto Company, Inc.Inventors: Takehiko Kataoka, Shinichi Kishimoto, Osahiro Sato
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Patent number: 5728862Abstract: A method is disclosed for preparing and purifying N-?N-(3,3-dimethylbutyl)-L-.alpha.-aspartyl!-L-phenylalanine 1-methyl ester from aspartame and 3,3-dimethylbutyraldehyde by hydrogenation in an organic solvent solution followed by the formation of an aqueous/organic solvent solution having an organic solvent content of about 17% to about 30% by weight of the aqueous/organic solvent solution.Type: GrantFiled: January 29, 1997Date of Patent: March 17, 1998Assignee: The NutraSweet CompanyInventor: Indra Prakash
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Patent number: 5723651Abstract: An economical process for producing .alpha.-L-aspartyldipeptide amide derivatives useful as sweeteners, by using amino protecting groups which can be removed by hydrolysis under acidic conditions, resulting in conversion of a .beta.-carboxyl acid ester to a carboxylic acid.Type: GrantFiled: December 28, 1995Date of Patent: March 3, 1998Assignee: Ajinomoto Co., Inc.Inventors: Toyoto Hijiya, Tadashi Takemoto, Ryoichiro Nakamura, Yusuki Amino, Naoko Sugiyama
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Patent number: 5723459Abstract: The present invention relates to novel compounds which possess a broad range of useful biological activities. These compounds can maintain, increase, or restore sensitivity of cells to therapeutic or prophylactic agents. They can also suppress, modify, or significantly reduce an immune response, including an autoimmune response in a mammal. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well-suited for treatment of multi-drug resistant cells, for prevention of the development of multi-drug resistance, for use in multi-drug resistant cancer therapy, and for prevention or treatment of graft rejection and various autoimmune diseases.Type: GrantFiled: January 24, 1995Date of Patent: March 3, 1998Assignee: Vertex Pharmaceuticals IncorporatedInventors: David M. Armistead, Matthew W. Harding, Jeffrey O. Saunders, Joshua S. Boger
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Patent number: 5714632Abstract: A compound of the formula ##STR1## wherein Q is an organic group of at least two carbon atoms having at least m substituents,m is 1, 2, 3, 4, 5 or 6, andn is 0 or 1.R.sup.3 is H or methyl,R.sup.8 and R.sup.9 are independently hydrogen, alkyl group or aryl,R.sup.12 and R.sup.13 are independently selected from the group consisting of an alkyl group or a cation, andR.sup.10 is independently selected from the group consisting of hydrogen, an alkyl group, aryl group, and highly-fluorinated alkyl group,R.sup.4 may be hydrogen or alkyl group, andR.sup.7 may be hydrogen or lower alkyl group, provides excellent stability to dispersions.Type: GrantFiled: November 13, 1995Date of Patent: February 3, 1998Assignee: Minnesota Mining And Manufacturing CompanyInventors: Prabhakara S. Rao, Larry R. Krepski, Terrance P. Smith
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Patent number: 5705529Abstract: The invention relates to novel N-benzoylamino acid derivatives of the general formula (I), ##STR1## wherein R.sup.1 and R.sup.2, which are the same or different, stand for a hydroxyl group optionally bearing an acetyl group; or a C.sub.1-6 alkoxy group optionally substituted by a phenyl group;n means an integer from 2 to 15as well as their tautomers, racemates and optically active individual (pure) isomers or mixtures thereof and the salts of these compounds and pharmaceutical compositions containing these compounds.The invention relates also to a process for the preparation of compounds of the general formula (I).Type: GrantFiled: October 11, 1995Date of Patent: January 6, 1998Assignee: Gyogyszerkutato Intezet KFTInventors: Peter Matyus, Erzsebet Zara, Lajos Farkas, Agnes Papp, Antal Simay, Lajos Toldy, Ferenc Andrasi, Katalin Goldschmidt, Eszter Hodula, Ildiko Mathe, Klara Sutka, Zsuzsanna Fittler, Valeria Vitkoczi, Laszlo Sebestyen, Istvan Sziraki, Marta Rusz, Eva Gal
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Patent number: 5693320Abstract: Novel acetylsalicylic acid derivatives having general formula (I) are provided, in which R.sup.1 is hydrogen or methyl; R.sup.2 is --O-- or --NH--; and W is hydroxy, halogen, lower alkoxy, lower alkenyloxy, lower alkynyloxy, cycloalkyloxy, aryloxy, aralkyloxy, acyloxy, or --N(R.sup.3)(R.sup.4) wherein the lower alkoxy, the lower alkenyloxy, the lower alkynyloxy, the cycloalkyloxy, the aryloxy, the aralkyloxy, and the acyloxy are optionally substituted with hydroxy, carboxyl, lower alkoxy, lower alkyl, halogen, nitro, and amino. The invention also pertains to a polymer made from such derivatives and a medical equipment containing the polymer. The polymer is useful in the prevention of platelet aggregation thereon.Type: GrantFiled: March 12, 1996Date of Patent: December 2, 1997Assignee: Ube Industries, Ltd.Inventors: Masamune Sakai, Hiroyuki Ikeda, Noriaki Kaneko, Yutaka Tamura
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Patent number: 5693617Abstract: Disclosed herein is a method for reducing the rate of degradation of proteins in an animal comprising contacting cells of the animal with certain proteasome inhibitors. The structure of the inhibitors are also disclosed.Type: GrantFiled: January 15, 1995Date of Patent: December 2, 1997Assignee: ProScript, Inc.Inventors: Ross L. Stein, Yu-Ting Ma, Stephen Brand
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Patent number: 5693485Abstract: The invention relates to a process for the preparation of N-protected-L-aspartyl-L-phenylalanine methyl ester by enzymatic coupling of an N-protected-L-aspartic acid and L- or DL-phenylalanine methyl ester in an aqueous solution with formation of a precipitate using a thermolysin-like protease enzyme, wherein a water-immiscible organic solvent is added to and blended with the reaction system during the formation of the precipitate in the course of the coupling reaction, which organic solvent has a relatively high affinity for the precipitate. The process is particularly suitable as a continuous process. The method results in lower enzyme deactivation during and after the enzymatic coupling reaction and in larger and thicker precipitated crystals.Type: GrantFiled: October 11, 1996Date of Patent: December 2, 1997Assignee: Holland Sweetener Company V.o.F.Inventors: Tsuneo Harada, Shigeaki Irino, Yukio Kunisawa, Kiyotaka Oyama
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Patent number: 5670684Abstract: The present invention provides novel intermediates which are useful for the preparation of excitatory amino acid receptor antagonists. Further provided is a process to enatioselectively prepare hydroisoquinoline compounds with central nervous system activity.Type: GrantFiled: May 19, 1995Date of Patent: September 23, 1997Assignee: Eli Lilly and CompanyInventors: Anita Melikian-Badalian, Paul L. Ornstein
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Patent number: 5670650Abstract: Novel derivatives of fatty acid analogs that have from one to three heteroatoms in the fatty acid moiety which can be oxygen, sulfur or nitrogen, are disclosed in which the carboxy-terminus has been modified to form various amides, esters, ketones, alcohols, alcohol esters and nitriles thereof.These compounds are useful as substrates for N-myristoyltransferase (NMT) and/or its acyl coenzyme, and as anti-viral and anti-fungal agents or pro-drugs of such agents. Illustrative of the disclosed compounds are fatty acid amino acid analogs of the structure ##STR1## in which X is the ethyl or t-butyl ester of an amino acid such as Gly, L-Ala, L-Ile, L-Phe, L-Trp, L-Thr or an amide such as NHCH.sub.2 C.sub.6 H.sub.5 or NH(CH.sub.2).sub.2 C.sub.6 H.sub.5.Type: GrantFiled: November 4, 1996Date of Patent: September 23, 1997Assignee: G. D. Searle & Co.Inventors: Sean T. Nugent, Richard A. Mueller
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Patent number: 5665774Abstract: This invention relates to a novel class of immunosuppressive compounds having an affinity for the FK-506 binding protein (FKBP). Once bound to this protein, the immunosuppressive compounds inhibit the prolyl peptidyl cis-trans isomerase (rotamase) activity of the FKBP and inhibit T cell activation. As such, the compounds of this invention can be used as immunosuppressive drugs to prevent or significantly reduce graft rejection in bone marrow and organ transplantations and for use in the treatment of a wide variety of autoimmune diseases in humans and other mammals.Type: GrantFiled: March 8, 1993Date of Patent: September 9, 1997Inventors: David M. Armistead, Joshua S. Boger, Harold V. Meyers, Jeffrey O. Saunders, Roger D. Tung
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Patent number: 5663435Abstract: Reaction products of amino-alkylenecarboxylic acids with polyoxyalkylene compounds are used as paraffin dispersants for mineral oil middle distillates.Type: GrantFiled: November 29, 1995Date of Patent: September 2, 1997Assignee: BASF AktiengesellschaftInventors: Gabriele Dralle-Voss, Knut Oppenlander, Klaus Barthold, Bernd Wenderoth, Wolfgang Kasel
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Patent number: 5659066Abstract: Described herein is a method for crystallizing aspartame (APM) by cooling an aqueous solution containing APM without forced convection during part of the crystallization, wherein a clear aqueous APM solution is initially cooled under forced convection and forced convection is interrupted, after crystallization has started but before the concentration of the APM crystals formed in the system reaches 0.5% by weight, until the amount of crystals reaches at least 10%, but not more than 50%, of the target amount, and wherein cooling is interrupted for at least part of the time of said interruption of forced convection at about the same time or shortly thereafter.Type: GrantFiled: March 20, 1996Date of Patent: August 19, 1997Assignee: Holland Sweetner Company V.o.F.Inventors: Tsugio Murakami, Hidetaka Egashira, Kengo Okajima, Hidetoshi Wakamatsu
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Patent number: 5650508Abstract: 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: July 22, 1997Assignee: Georgia Tech Research CorporationInventor: James C. Powers
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Patent number: 5643552Abstract: This invention relates to methods of x-ray diagnostic imaging the blood pool, liver, spleen, and/or lymph system of a mammal comprising administering a contrast effective amount of a mixed carbonic anhydride as a contrast agent having the structure ##STR1## X is H, NR.sup.1 R.sup.2 or CONR.sup.1 R.sup.3, R.sup.1 is H or alkylR.sup.2 is COR.sup.3R.sup.3 is H, alkyl, hydroxyl-substituted alkyl, aryl or a steroidially derived moietyY is NR.sup.1 R.sup.2 or CONR.sup.1 R.sup.3 and ##STR2## Z is OR.sup.3 or This invention further relates to novel mixed carbonic anhydride contrast agents having the above structure and to x-ray contrast compositions comprising such agents, and to methods of x-ray diagnostic imaging utilizing such agents.Type: GrantFiled: August 22, 1995Date of Patent: July 1, 1997Assignee: NanoSystems L.L.C.Inventor: Carl R. Illig
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Patent number: 5639746Abstract: The invention provides hydroxamic acid-containing compounds which are useful as inhibitors of matrix metalloproteases and which are effective in treating conditions associated with excess activity of these enzymes. In particular, the present invention relates to a compound having a structure according to Formula I ##STR1## wherein (A)R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently selected from various substituents; and(B) where R.sup.3 and R.sup.4 or R.sup.4 and R.sup.5 may together comprise a cyclic moiety; or a pharmaceutically-acceptable salt, biohydrolyzable amide or biohydrolyzable ester thereof.In other aspects, the invention is directed to pharmaceutical compositions containing the compounds of Formula (I), and to methods of treating diseases characterized by matrix metalloprotease activity using these compounds or the pharmaceutical compositions containing them.Type: GrantFiled: December 29, 1994Date of Patent: June 17, 1997Assignee: The Procter & Gamble CompanyInventor: Kenneth Edward Yelm
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Patent number: 5639789Abstract: Novel butadiene derivatives of the formula [I]: ##STR1## wherein Ring A is tri-lower alkoxyphenyl, R.sup.1 and R.sup.2 combine each other to form a group of the formula: ##STR2## or one of R.sup.1 and R.sup.2 is lower alkoxy, and the other is group of the formula: -NHR.sup.3, in which R.sup.3 is hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkoxy, substituted or unsubstituted amino, hydroxy or pyridylcarbonyl, or salts thereof, these compounds have excellent antithrombotic activity and are useful as antithrombotic drug, or synthetic intermediate for preparing other antithrombotic drug.Type: GrantFiled: May 8, 1995Date of Patent: June 17, 1997Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Tameo Iwasaki, Takashi Nishitani, Akio Ohtani, Masanori Inamasu
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Patent number: 5637754Abstract: A method for crystallizing aspartame comprising the combination of steps of: (A) providing (i) dispersed droplets of a fluid mixture comprising aspartame and water, and (ii) a water-immiscible fluid zone; (B) passing the dispersed droplets through the water-immiscible fluid zone under effective temperature and dispersive conditions to effect cooling of the dispersed droplets so that a state of initial relative supersaturation of aspartame between about 1 and 6 is formed within the dispersed droplets; (C) collecting the dispersed droplets in the supersaturated state in a substantially static collection zone so that a slurry comprising a crystalline form of aspartame is formed from the droplets. The method provides for rapid, efficient cooling of aspartame solutions and yields aspartame crystals with desirable qualities.Type: GrantFiled: December 20, 1995Date of Patent: June 10, 1997Assignee: Holland Sweetener Co., V.o.F.Inventors: Marinus P. W. M. Rijkers, Antoon G. T. Toussaint, Alexander P. M. Vrinzen
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Patent number: 5637701Abstract: A novel asymmetric synthesis is provided for preparing optically active amides of formula (A) and their salts. ##STR1## In the formula, X represent --N-- or --CH--, R represents a mono or bicyclic aryl or heteroaryl group, R.sup.1 is an aryl or heteroaryl radical, and R.sup.2 and R.sup.3 have specified meanings. The products are useful as 5-HT.sub.1A antagonists.Novel diesters of formula D useful as intermediates in the process are also disclosed.Type: GrantFiled: April 11, 1995Date of Patent: June 10, 1997Assignee: John Wyeth & Brother, LimitedInventor: Mark A. Ashwell
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Patent number: 5629346Abstract: Certain N-acetonylbenzamides exhibit low toxicity to plants are particularly useful for control of fungi, especially Phycomycetes.Type: GrantFiled: June 6, 1995Date of Patent: May 13, 1997Assignee: Rohm and Haas CompanyInventors: H. Edwin Carley, Ashok K. Sharma, Colin Swithenbank