Phenylalanines Patents (Class 560/40)
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Patent number: 7026003Abstract: The present invention provides processes for preparing a slurry containing aspartame, which is stable and is useful as a sweetener; as well as methods of assessing the stability of an aspartame slurry.Type: GrantFiled: November 21, 2002Date of Patent: April 11, 2006Assignee: Ajinomoto Co., Inc.Inventors: Yasuyuki Tomiyama, Masato Kawauchi
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Patent number: 6989461Abstract: Catalyst for the asymmetric (transfer) hydrogenation represented by the formula MLaXbSc, where M is a transition metal, to be chosen from rhodium and ruthenium, and X is a counter ion and S is a ligand, a ranges from 0.5 to 3 and b and c, each independently, range from 0 to 2, and L is a chiral ligand having the formula (1), where Cn together with the two 2 O-atoms and the P-atom forms a substituted or non-substituted ring with 2-4 C-atoms, R1 and R2 each independently represent H, an optionally substituted alkyl, aryl, alkaryl or aralkyl group or may form a (heterocyclic) ring together with the N-atom to which they are bound. And a process for the asymmetric (transfer) hydrogenation of an olefinically unsaturated compound, ketone, imine or oxime derivate in the presence of a hydrogen donor and of a catalyst, use being made of a catalyst represented by formula MLaXbSc, where M is a transition metal, to be chosen from rhodium, iridium and ruthenium, X is a counter ion, S is a ligand, a ranges from 0.Type: GrantFiled: July 6, 2001Date of Patent: January 24, 2006Assignee: DSM IP Assets B.V.Inventors: Michel Berg Van Den, Ben Feringa, Adriaan Jacobus Minnaard, Johannes Gerardus Vries De
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Patent number: 6939987Abstract: N-[N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-?-aspartyl]-L-phenylalanine 1-methyl ester is prepared by a process comprising: subjecting Aspartame and 3-(3-methoxy-4-hydroxyphenyl)propionaldehyde or derivatives thereof to reductive alkylation in a solvent to produce N-[N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-?-aspartyl]-L-phenylalanine 1-methyl ester; and crystallizing said compound.Type: GrantFiled: September 8, 2003Date of Patent: September 6, 2005Assignee: Ajinomoto Co., Inc.Inventors: Yusuke Amino, Kazuko Yuzawa, Tadashi Takemoto
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Patent number: 6930200Abstract: Mono-substituted and di-substituted alpha-amino acids and derivatives thereof, substituted at the alpha positon with one (mono-) or two (di-) substituents (R2 and/or R3) as shown in Formula 1: N(R4R5)C(R2R3)CO(OR1).Type: GrantFiled: June 26, 2003Date of Patent: August 16, 2005Assignee: Pharmacore, Inc.Inventor: Adnan M. M. Mjalli
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Patent number: 6919380Abstract: Derivatives of C2-substituted indan-1-ol compounds of formula I: its physiologically acceptable salts, and its physiologically functional derivatives for the prophylaxis or treatment of obesity are disclosed herein. Compositions comprising the same, methods for preparing the instant compounds, and methods for reducing weight in mammals and for the prophylaxis or treatment of obesity are also described.Type: GrantFiled: October 27, 2003Date of Patent: July 19, 2005Assignee: Aventis Pharma Deutschland GmbH.Inventors: Gerhard Jaehne, Volker Krone, Martin Bickel, Matthias Gossel
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Patent number: 6914151Abstract: A crystallization process for forming a stable crystal of N-(3,3-dimethylbutyl)-APM, which comprises using either water or a mixture of water with a lower alcohol as the crystallizing solvent and controlling the crystallization point to 30° C. or above; and another crystallization process therefor, which comprises using either water or a mixture of water with a lower alcohol as the crystallizing solvent and using as the seed crystal a crystal of N-(3,3-dimethylbutyl)-APM exhibiting peculiar peaks of diffracted X-ray at least at diffraction angles (2?, CuK? ray) of 6.0°, 24.8°, 8.2° and 16.5° to thereby crystallize the above objective crystal preferentially. These crystallization processes enable the constant formation of stable crystals of N-(3,3-dimethylbutyl)-APM at a low cost.Type: GrantFiled: November 1, 1999Date of Patent: July 5, 2005Assignee: Ajinomoto Co., Inc.Inventors: Shigeru Kawahara, Akihiro Kishishita, Kazutaka Nagashima, Tadashi Takemoto
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Patent number: 6899912Abstract: N-[N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-?-aspartyl]-L-phenylalanine 1-methyl ester is prepared by a process comprising: subjecting Aspartame and 3-(3-methoxy-4-hydroxyphenyl)propionaldehyde or derivatives thereof to reductive alkylation in a solvent to produce N-[N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-?-aspartyl]-L-phenylalanine 1-methyl ester; and crystallizing said compound.Type: GrantFiled: March 7, 2002Date of Patent: May 31, 2005Assignee: Ajinomoto Co., Inc.Inventors: Yusuke Amino, Kazuko Yuzawa, Tadashi Takemoto
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Patent number: 6855843Abstract: The present invention relates to a pharmaceutical composition comprising as an active ingredient a compound of formula (I), wherein Ring A is an aromatic or a heterocyclic ring; Q is a bond, carbonyl, lower alkylene, lower alkenylene, —O— -(lower alkylene)-, etc.; n is 0, 1 or 2; Z is oxygen or sulfur; W is oxygen, sulfur, —CH?CH—, —NH— or —N?CH—; R1, R2 and R3 are the same or different and are hydrogen, halogen, hydroxyl, a substituted or unsubstituted lower alkyl gorup, a substituted or unsubstituted lower alkoxy group, a substituted or unsubstituted amino group, etc.; R4 is tetrazolyl, carboxyl group, amide or ester; R5 is hydrogen, nitro, amino, hydroxyl, lower alkanoyl, lower alkyl, etc.; R6 is selected from (a) a substituted or unsubstituted phenyl group, (b) a substituted or unsubstituted pyridyl group, (c) a substituted or unsubstituted thienyl group, (d) a substituted or unsubstituted benzofuranyl group, etc.; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: November 4, 2002Date of Patent: February 15, 2005Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Ila Sircar, Kristjan S. Gudmundsson, Richard Martin
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Patent number: 6852875Abstract: Synthesis of N-[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester by treating N-(3,3-dimethylbutyl)-L-aspartic acid with ketones to give oxazolidinone derivatives, which are condensed with L-phenylalanine methyl ester.Type: GrantFiled: May 18, 2001Date of Patent: February 8, 2005Assignee: The Nutrasweet Co.Inventor: Indra Prakash
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Patent number: 6844465Abstract: Disclosed in the present application are a method for preparing highly-stable A-type crystals by controlling and maintaining the product temperature of B-type N-(3,3-dimethylbutyl)-APM crystals at 25 to 80° C. under an absolute humidity of 0.203 kg/kg or less environment, thereby effecting crystal transition; and a method for preparing A-type crystals by controlling and maintaining the product temperature of D-type crystals of N-(3,3-dimethylbutyl)-APM at 25 to 80° C. under an absolute humidity of 0.0550 kg/kg or less environment, thereby effecting crystal transition. According to these crystal transition methods, highly stable crystals can be prepared stably and at a low cost.Type: GrantFiled: June 4, 2002Date of Patent: January 18, 2005Assignee: Ajinomoto Co., Inc.Inventors: Shigeru Kawahara, Akihiro Kishishita, Kazutaka Nagashima, Tadashi Takemoto
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Patent number: 6841183Abstract: N-[N-[3-(2-hydroxy-substituted phenyl)propyl]-L-?-aspartyl]-L-phenylalanine 1-methyl ester derivatives, which are useful as sweeteners, may be conveniently produced by subjecting a 2-hydroxychroman derivative having various substituents on the benzene ring and aspartame to a reductive alkylation reaction. These compounds may be purified by subjecting such a derivative containing one or more impurities to a crystallization step to crystallize the same. Further, there are provided a process for producing dialkoxychroman derivatives useful as intermediates for the production of such aspartame derivatives in the above process, and novel dialkoxychroman derivatives thus produced, which are excellent as the production intermediate.Type: GrantFiled: March 29, 2002Date of Patent: January 11, 2005Assignee: Ajinomoto Co., Inc.Inventors: Kazutaka Nagashima, Shinji Fujita, Yuuichi Aoki, Shigeru Kawahara, Tadashi Takemoto, Eriko Ono
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Publication number: 20040236140Abstract: N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of L-&agr;-aspartyl-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde produced in situ by the hydrolysis or cleavage of a 3,3-dimethylbutyraldehyde precursor. The production method is efficient and low cost, as compared with conventional N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester synthesis.Type: ApplicationFiled: April 30, 2004Publication date: November 25, 2004Applicant: NUTRASWEET COMPANYInventors: Indra Prakash, Kenneth E. Furlong, Handley E. Jackson
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Patent number: 6822111Abstract: N-[N-[3-(phenyl having various substituent group(s) on the benzene ring)propyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester derivatives, which are useful as sweeteners, may be conveniently produced on an industrial scale at a high yield by reductively alkylating aspartame with a 3-(phenyl having specified substituent group(s) on the benzene ring)-2-propenyl aldehyde and hydrogen in the presence of a catalyst and a base.Type: GrantFiled: November 4, 2002Date of Patent: November 23, 2004Assignee: Ajinomoto Co., Inc.Inventors: Shigeru Kawahara, Kazutaka Nagashima, Tadashi Takemoto
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Publication number: 20040230073Abstract: The present invention relates to a method of manufacturing aspartyl dipeptide ester compounds, which can be used as sweeteners.Type: ApplicationFiled: June 8, 2004Publication date: November 18, 2004Applicant: Ajinomoto Co., Inc.Inventors: Shigeru Kawahara, Kazutaka Nagashima, Kenichi Mori, Tadashi Takemoto, Eriko Ono
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Patent number: 6818243Abstract: N-[N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester useful as a sweetener with a high potency of sweetness, is provided in the crystalline form having a high stability and a good purity which is favorable as a commercial product.Type: GrantFiled: June 28, 2002Date of Patent: November 16, 2004Assignee: Ajinomoto Co., Inc.Inventors: Kazutaka Nagashima, Yuuichi Aoki, Eriko Ono, Tadashi Takemoto
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Patent number: 6812256Abstract: Polysubstituted indan-1-ol compounds of formula I, its physiologically acceptable salts and physiologically functional derivatives are disclosed Compositions comprising the same, methods of preparation and methods for the prophylaxis or treatment of obesity are also disclosed herein.Type: GrantFiled: October 27, 2003Date of Patent: November 2, 2004Assignee: Aventis Pharma Deutschland GmbHInventors: Gerhard Jaehne, Volker Krone, Martin Bickel, Matthias Gossel
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Publication number: 20040192954Abstract: The compound O-(2-[18F]fluoroethyl)-L-tyrosine has proven to be particularly suitable for positron emission tomography and has already been tested in clinical practice. Until now, the compound has been prepared according to a relatively laborious method (Wester H. J. et al., J. Nucl. Med. 1999; 40: 205-212).Type: ApplicationFiled: May 24, 2004Publication date: September 30, 2004Inventor: Kurt Hamacher
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Patent number: 6794531Abstract: The present invention relates to a method of manufacturing aspartyl dipeptide ester compounds, which can be used as sweeteners, and aldehydes that can be used in the manufacturing processes.Type: GrantFiled: April 8, 2002Date of Patent: September 21, 2004Assignee: Ajinomoto Co., Inc.Inventors: Kazutaka Nagashima, Yuuichi Aoki, Tadashi Takemoto, Yusuke Amino, Nao Funakoshi, Eriko Ono
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Patent number: 6790470Abstract: For example, N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine methyl ester (A-type crystal) showing characteristic peaks in diffractive X-ray at diffraction angles (2&thgr;, CuK&agr; ray) of at least 6.0°, 24.8°, 8.2° and 16.5° is dried to its water content below 3% by weight. The crystal thus dried is a novel crystal (C-type crystal) of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine methyl ester excellent in dissolution rate, and when measured by powder X-ray diffractometry, this crystal shows characteristic peaks in diffractive X-ray at diffraction angles (2&thgr;, CuK&agr; ray) of at least 7.1°, 19.8°, 17.3° and 17.7°. The dissolution rate (solubility) of the C-type crystals is further improved by converting the crystals into granules.Type: GrantFiled: November 8, 2000Date of Patent: September 14, 2004Assignee: Ajinomoto Co., Inc.Inventors: Akihiro Kishishita, Kazutaka Nagashima, Hirotoshi Ishida, Takeshi Nagai
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Patent number: 6784309Abstract: This invention relates to the purification of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester by slurrying a mixture containing N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester with organic or aqueous organic solvents.Type: GrantFiled: April 14, 2000Date of Patent: August 31, 2004Assignee: The Nutrasweet CompanyInventors: Indra Prakash, Kurt Wachholder
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Patent number: 6767572Abstract: The present invention relates to a method of manufacturing aspartyl dipeptide ester compounds, which can be used as sweeteners.Type: GrantFiled: April 8, 2002Date of Patent: July 27, 2004Assignee: Ajinomoto Co., Inc.Inventors: Shigeru Kawahara, Kazutaka Nagashima, Kenichi Mori, Tadashi Takemoto, Eriko Ono
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Publication number: 20040137559Abstract: The present invention relates to a novel process for producing an N-formyl-neutral-amino acid and N-formylaspartic acid. The present invention also relates to a novel process for producing N-formyl-&agr;-L-aspartyl-L-phenylalanine methyl ester as a precursor of aspartame and aspartame, as well as a method of making a precursor of aspartame and aspartame by using the same.Type: ApplicationFiled: October 20, 2003Publication date: July 15, 2004Applicant: Ajinomoto Co., Inc.Inventors: Shigeru Kawahara, Tadashi Takemoto, Shinji Fujita, Ayako Ohno
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Patent number: 6720446Abstract: Processes for using modified catalysts with improved functionality in the production of neotame are disclosed. The modified catalysts surprisingly have been found to improve the selectivity over conventional catalysts and to reduce the level of certain impurities in neotame production processes.Type: GrantFiled: November 5, 2001Date of Patent: April 13, 2004Assignee: The NutraSweet CompanyInventors: Mike G. Scaros, Indra Prakash
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Publication number: 20040049066Abstract: N-[N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is prepared by a process comprising:Type: ApplicationFiled: September 8, 2003Publication date: March 11, 2004Applicant: AJINOMOTO CO. INCInventors: Yusuke Amino, Kazuko Yuzawa, Tadashi Takemoto
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Patent number: 6689902Abstract: 3-(3-Methyl-4-hydroxyphenyl)-3-methylbutyl aldehyde may be produced from 3-(3-methyl-4-hydroxyphenyl)-3-methylbutyric acid by converting the carboxyl group into a formyl group. N-[N-[3-(3-methyl-4-hydroxyphenyl)-3-methylbutyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester, which is useful as a sweetener having a high potency of sweetness, can be easily and efficiently prepared on an industrial production from such an aldehyde derivative, via a reductive alkylation reaction with aspartame. Therefore, 3-(3-Methyl-4-hydroxyphenyl)-3-methylbutyl aldehyde is extremely excellent as an intermediate for the production of N-[N-[3-(3-methyl-4-hydroxyphenyl)-3-methylbutyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester.Type: GrantFiled: July 19, 2002Date of Patent: February 10, 2004Assignee: Ajinomoto Co., Inc.Inventors: Kenichi Mori, Shigeru Kawahara, Tadashi Takemoto
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Patent number: 6657073Abstract: The present invention provides a novel process for the crystallization of &agr;-L-aspartyl-L-phenylalanine methyl ester crystals wherein initial nucleation and initial crystal growth is conducted in a controlled manner in a metastable supersaturated solution, followed by further crystal growth via a cooling crystallization step. The process disclosed herein can be performed in an industrial scale.Type: GrantFiled: September 1, 2000Date of Patent: December 2, 2003Assignee: Daesang CorporationInventor: Cheong-Song Choi
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Publication number: 20030216592Abstract: The present invention relates to a 3-substituted-phenyl-3-merthylbutyric acid and 3-substituted-phenyl-3-merthylaldehyde derivatives, which are useful in the production of N-[N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester, which is a sweetener with high sweetening potency.Type: ApplicationFiled: May 20, 2002Publication date: November 20, 2003Applicant: AJINOMOTO CO., INC.Inventors: Shigeru Kawahara, Kenichi Mori, Kazutaka Nagashima, Tadashi Takemoto
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Patent number: 6642406Abstract: N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of a mixture of 3,3-dimethylbutyraldehyde and a precursor of L-&agr;-aspartyl-L-phenylalanine 1-methyl ester. In particular, N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is produced using an acid salt of L-&agr;-aspartyl-L-phenylalanine 1-methyl ester or N-protected L-&agr;-aspartyl-L-phenylalanine 1-methyl ester. The production method is efficient and low cost, as compared with conventional N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester synthesis.Type: GrantFiled: May 18, 2001Date of Patent: November 4, 2003Assignee: The NutraSweet CompanyInventors: Indra Prakash, Zhi Guo, Steve Schroeder, Kurt L. Wachholder
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Patent number: 6627431Abstract: A chemoenzymatic method is disclosed for preparing N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester via the enzymatic regioselective hydrolysis of neotame esters using lipases or esterases.Type: GrantFiled: May 12, 2000Date of Patent: September 30, 2003Assignee: The NutraSweet CompanyInventors: Indra Prakash, Robert Y. Zhao
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Patent number: 6613933Abstract: A process for easily and efficiently separating aspartame (APM) from N-[N-(3,3-dimethylbutyl)-L-(&agr;-aspartyl]-L-phenylalanine methyl ester (APM derivative), and thus separating and purifying the APM and the above-mentioned APM derivative, more specifically the N-(3,3-dimethylbutyl)-APM each at a high purity, which comprises subjecting an aqueous solution containing the APM and the APM derivative, to column chromatography using a nonpolar highly porous polymer based resin.Type: GrantFiled: June 9, 2000Date of Patent: September 2, 2003Assignee: Ajinomoto Co., Inc.Inventors: Kazutaka Nagashima, Akihiro Kishishita
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Patent number: 6610710Abstract: Phenylalanine derivatives of the following formula and analogues thereof have an antagonistic activity to &agr;4&bgr;7 integrin and a selectivity toward &agr;4&bgr;1 integrin. They are used as therapeutic agents for various diseases to which &agr;4&bgr;7 integrin relates.Type: GrantFiled: June 28, 2002Date of Patent: August 26, 2003Assignee: Ajinomoto Co., Inc.Inventors: Yasuhiro Tanaka, Toshihiko Yoshimura, Chieko Ejima, Mitsuhiko Kojima, Eiji Nakanishi, Hiroyuki Izawa, Yuko Satake, Nobuyasu Suzuki, Manabu Suzuki, Masahiro Murata
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Patent number: 6562782Abstract: The present invention related to an oligocycloalkanoid compound comprising formula (I) wherein m, n, and o are independently an integer from 0 to 2; A1 through A10 are independently a direct link, alkylene, alkylene-O—, carbonyl, oxygen, or sulfur; X and Y are independently hydrogen, hydroxy, alkyl, or in combination an electrophilic group; and R1 through R10 are independently hydrogen, hydroxy, alkyl, alkenyl, alkynyl, substituted or unsubstituted aryl, N-, S-, or O-heterocycles, fused or multi-ring aryl with or without hetero ring members, arylalkyl, arylalkenyl, arylalkynyl, alkylphenyl, alkenylphenyl, alkynylphenyl, alkoxy, alkenyloxy, alkynyloxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylalkoxy, alkylacyl, alkenylacyl, alkynylacyl, arylacyl, aroyl, alkylaroyl, aminoaroyl, aminoalkylacyl, aminoalkyl, aminoalkenyl, aminoalkynyl, amino, alkylamino, alkenylamino, alkynylamino, arylamino, dialkylamino, dialkenylamino, dialkynylamino, arylalkylamino, arylalkType: GrantFiled: May 10, 2000Date of Patent: May 13, 2003Assignee: University of RochesterInventors: Benjamin L. Miller, Robert D. Hubbard
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Patent number: 6552061Abstract: Provided are an anti-inflammatory agent containing, as an active ingredient, at least one selected from amino acid derivatives represented by formula (I) wherein Ar represents an optionally substituted 2-hydroxyaryl group, n is 0 or 1, R2 represents a hydrogen atom or a side chain of an &agr;-amino acid or &bgr;-amino acid, X represents —O— or —NH—, R1 represents a hydrogen atom or a group that forms, together with R2 and an adjacent atoms, a cyclic structure of pyroglutamic acid, and R3 represents a hydrogen atom, an alkyl group having from 1 to 22 carbon atoms or an alkenyl group having from 2 to 22 carbon atoms, and salts thereof, and toiletries or skin external products containing the same. The anti-inflammatory agent of the invention inhibits expression of an inflammatory protein and activation of a gene transcription control factor that participates therein, and exhibits a good feeling upon use and a safety.Type: GrantFiled: April 2, 1999Date of Patent: April 22, 2003Assignee: Ajinomoto Co., Inc.Inventors: Manabu Kitazawa, Keiji Iwasaki, Eiji Shiojiri
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Patent number: 6506434Abstract: The present invention relates to a process for coating N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester onto a carrier. The invention also relates to N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester coated carrier compositions.Type: GrantFiled: August 4, 2000Date of Patent: January 14, 2003Assignee: The NutraSweet CompanyInventors: Allan Towb, Douglas Nolte
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Publication number: 20020193621Abstract: Disclosed in the present application are a method for preparing highly-stable A-type crystals by controlling and maintaining the product temperature of B-type N-(3,3-dimethylbutyl)-APM crystals at 25 to 80° C. under an absolute humidity of 0.203 kg/kg or less environment, thereby effecting crystal transition; and a method for preparing A-type crystals by controlling and maintaining the product temperature of D-type crystals of N-(3,3-dimethylbutyl)-APM at 25 to 80° C. under an absolute humidity of 0.0550 kg/kg or less environment, thereby effecting crystal transition. According to these crystal transition methods, highly stable crystals can be prepared stably and at a low cost.Type: ApplicationFiled: June 4, 2002Publication date: December 19, 2002Applicant: Ajinomoto Co., Inc.Inventors: Shigeru Kawahara, Akihiro Kishishita, Kazutaka Nagashima, Tadashi Takemoto
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Patent number: 6495597Abstract: Compounds of formula (I) wherein R4 is an ester or thioester group and R, R1, R2 and R3 are as defined in the specification, inhibit proliferation of tumor cells.Type: GrantFiled: October 5, 2000Date of Patent: December 17, 2002Assignee: British Biotech Pharmaceuticals Ltd.Inventors: Andrew Paul Ayscough, Lisa Marie Pratt, Alan Hastings Drummond
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Publication number: 20020151668Abstract: A multi-dimensional copolymer array of a plurality of copolymers, polymerized from at least two independently variable sets of monomers, wherein the polymerization is characterized by:Type: ApplicationFiled: April 13, 1999Publication date: October 17, 2002Inventors: KEN JAMES, BROCCHINI STEPHEN, VARAWUT TANGPASUTHADOL, JOACHIM KOHN
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Patent number: 6465677Abstract: The synthesis of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester via conversion under reducing conditions of novel imidazolidinone(s) is disclosed.Type: GrantFiled: November 17, 1999Date of Patent: October 15, 2002Assignee: The NutraSweet CompanyInventors: Vladislav Orlovski, Indra Prakash, Mike G. Scaros, Christine M. V. Moore
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Publication number: 20020147361Abstract: N-[N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is prepared by a process comprising:Type: ApplicationFiled: March 7, 2002Publication date: October 10, 2002Applicant: AJINOMOTO CO. INCInventors: Yusuke Amino, Kazuko Yuzawa, Tadashi Takemoto
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Publication number: 20020128301Abstract: Non-nucleoside reverse transcriptase inhibitors of formula (P-1) wherein: Ar1 is an unsaturated, optionally substituted, mono or bicyclic ring structure comprising 0 to 3 hetero atoms selected from S, O and N; Ar2 is an aromatic, optionally substituted, monocyclic ring structure comprising at least one nitrogen hetero atom and zero to two further hetero atoms selected from S, O and N; R4 and R5 are independently H or C3-C8 cycloalkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C5 alkoxy, C1-C4 alkanoyloxy, C1-C4 alkylthio, amino, carboxy, carbamoyl, cyano, halo, hydroxy, aminomethyl, hydroxymethyl, carboxymethyl, or halo substituted C1-C6 alkyl mercapto, nitro; or R4 and RS join to form a 3-6 membered, optionally substituted ring structure; R6 is 0 or S; Rx is the residue of a natural or unnatural amino acid; and L* is a linker moiety which is ether-, carbonate- or ester-bound to the adjacent oxygen and ester linked to Rx; and pharmaceutically acceptable salts thereof are anti-HIV agents with favourable phType: ApplicationFiled: August 10, 2001Publication date: September 12, 2002Inventors: Xiao-Xiong Zhou, Nils-Gunnar Johansson, Horst Wahling, Christian Sund, Lourdes Salvador, Stefan Lindstrom, Hans Wallberg, Christer Sahlberg
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Patent number: 6444251Abstract: A homogeneous sweetener composition containing aspartame (APM) and N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine methyl ester having tasting properties similar to sucrose, can be efficiently produced in high yields and with a high purity by reductive alkylation of APM with an at most equimolar amount 3,3-dimethylbutylaldehyde followed by separating the reducing agent from the liquid reaction mixture, and separating of the precipitated crystals of the sweetener composition.Type: GrantFiled: June 15, 2000Date of Patent: September 3, 2002Assignee: Ajinomoto Co., Inc.Inventors: Akihiro Kishishita, Kazutaka Nagashima
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Patent number: 6423864Abstract: N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is crystallized in order to give highly pure product in high yield. In a preferred embodiment of the present invention, N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is crystallized directly from an aqueous methanol reaction mixture.Type: GrantFiled: November 24, 1999Date of Patent: July 23, 2002Assignee: The NutraSweet CompanyInventors: Indra Prakash, Christine M. V. Moore, Kurt Wachholder
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Patent number: 6417368Abstract: The invention provides a resin-immobilized imine represented by the following formula: P—Q—N—═CH—R I [in the formula, P represents the principal chain of a resin polymer; Q represents a substituted or unsubstituted hydrocarbon side chain or a substituted or unsubstituted hydrocarbon side chain with a heteroatom interposed therein; R represents a substituted or unsubstituted hydrocarbon group or heterocyclic group] and a resin-immobilized &bgr;-aminocarbonyl compound of the following formula: which can be released as &bgr;-aminocarbonyl compound from the solid phase; and the invention also provide a resin-immobilized amine of the following formula: —P—Q1—O—Q2—NH2 III [Q1 and Q2 independently represent a hydrocarbon chain such as arylene, alkylenearylene or arylenealkylene], which is essential for solid state synthesis; and the invention has enabled the solid state synthesis of &bgr;-amType: GrantFiled: November 8, 2000Date of Patent: July 9, 2002Assignee: Japan Science and Technology CorporationInventors: Shu Kobayashi, Yoji Aoki
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Patent number: 6372278Abstract: One embodiment of the present invention provides a sweetener composition, which includes N-{N-(3,3-dimethylbutyl)-L-&agr;-aspartyl}-L-phenylalanine 1-methyl ester, and Aspartame, wherein a ratio of the Aspartame to a total amount of the Aspartame and the N-{N-(3,3-dimethylbutyl)-L-&agr;-aspartyl}-L-phenylalanine 1-methyl ester is in the range of 10 to 99.5% by weight, methods of making and of using. Another embodiment of the present invention provides a method for preparing a sweetener composition, which includes drying an A-type crystal of N-{N-(3,3-dimethylbutyl)-L-&agr;-aspartyl }-L-phenylalanine 1-methyl ester to obtain a C-type crystal of N-{N-(3,3-dimethylbutyl)-L-&agr;-aspartyl }-L-phenylalanine 1-methyl ester.Type: GrantFiled: November 8, 2000Date of Patent: April 16, 2002Assignee: Ajinomoto Co., Inc.Inventors: Hirotoshi Ishida, Akihiro Kishishita, Takeshi Nagai, Kazutaka Nagashima, Atsuhiko Hirano
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Patent number: 6372279Abstract: One embodiment of the present invention provides a sweetener composition, which includes a mixture of N-{N-(3,3-dimethylbutyl)-L-&agr;-aspartyl}-L-phenylalanine 1-methyl ester, and Acesulfame K, wherein a ratio of the Acesulfame K to a total amount of the N-{N-(3,3-dimethylbutyl)-L-&agr;-aspartyl}-L-phenylalanine 1-methyl ester and the Acesulfame K is in the range of 10 to 97% by weight, methods of making and of using. Another embodiment of the present invention provides a method for preparing a sweetener composition, which includes drying an A-type crystal of N-{N-(3,3-dimethylbutyl)-L-&agr;-aspartyl}-L-phenylalanine 1-methyl ester to obtain a C-type crystal of N-{N-(3,3-dimethylbutyl)-L-&agr;-aspartyl}-L-phenylalanine 1-methyl ester.Type: GrantFiled: November 8, 2000Date of Patent: April 16, 2002Assignee: Ajinomoto Co., Inc.Inventors: Hirotoshi Ishida, Akihiro Kishishita, Takeshi Nagai, Kazutaka Nagashima, Atsuhiko Hirano
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Patent number: 6368651Abstract: This invention relates to the use of at least one taste modifying ingredient to modify at least one taste characteristic imparted by N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester, or neotame, compositions containing the same, and use of modified forms of neotame that possess an improved taste, wherein at least one taste characteristic imparted by neotame is positively affect by the modification of neotame.Type: GrantFiled: May 10, 2000Date of Patent: April 9, 2002Assignee: The NutraSweet CompanyInventors: Paula A. Gerlat, Gale C. Walters, Ihab E. Bishay, Indra Prakash, Tammy C. Jarrett, Nitin Desai, Harold A. Sawyer, Claire-Lise T. Bechert
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Patent number: 6365216Abstract: N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is converted from a light powder to relatively dustless, free-flowing particles with and without the use of binders using extrusion and spheronization processes. These particles are suitable for use in a variety of applications. Food products sweetened with extruded or spheronized N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and methods of sweetening food products with such N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester are also disclosed.Type: GrantFiled: March 24, 2000Date of Patent: April 2, 2002Assignee: The NutraSweet CompanyInventors: Aditi Dron, Ihab E. Bishay, Jim Fotos, Michael J. Trione
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Patent number: 6365217Abstract: This invention provides a process for preparing an agglomerate of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and a carrier including the steps of: (a) providing a premix solution containing N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and a binding agent; (b) fluidizing a carrier; and (c) applying the premix solution of step (a) onto said fluidized carrier to form an agglomerate of said N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and said carrier. This invention is also directed to the novel agglomerates prepared by the process of this invention.Type: GrantFiled: December 4, 2000Date of Patent: April 2, 2002Assignee: The Nutra Sweet CompanyInventors: Jim Fotos, Ihab Bishay
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Patent number: RE39088Abstract: An amide compound of the formula (I): ? wherein R is amino and the like, A is alkylene and the like, X is O, S and the like, M is arylene and the like, R1, R2, R3 and R4 are H, hydroxy and the like, R5 is H, alkyl and the like, m is an integer of 0-6, R6 is an optionally substituted aryl and the like, and R7 is H, an optionally substituted alkyl and the like, a pharmaceutically acceptable acid addition salt thereof and a pharmaceutical containing same as an active ingredient. The amide compounds exhibit superior suppressive effects on cytokines directly or indirectly involved in inflammations, such as IL-8, IL-1, IL-6, TNF-?, GM-CSF and the like, and are useful for the prophylaxis and treatment of rheumatic diseases, arthritis due to gout and the like.Type: GrantFiled: August 15, 1996Date of Patent: May 2, 2006Assignee: Japan Tobacco, Inc.Inventors: Junichi Haruta, Kazuhiko Sakuma, Yoshihiro Watanabe
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Patent number: RE37795Abstract: A method for preparing diphenol compounds, which method includes the steps of coupling a hydroxyphenyl carboxylic acid with a L-tyrosine ester in a water-miscible organic reaction solvent containing a carbodiimide capable of forming a water-soluble urea by-product, thereby forming a diphenol reaction product; and combining the reaction mixture with an amount of water effective to precipitate the diphenol as a water-immiscible organic phase, so that a water-immiscible organic phase is formed containing the diphenol reaction product. New diphenol monomers and polymers polymerized therefrom are also discussed.Type: GrantFiled: July 21, 1999Date of Patent: July 16, 2002Inventors: Joachim B. Kohn, Stephen Brocchini, Arthur L. Schwartz