Plural Nitrogens Patents (Class 562/448)
  • Patent number: 4873253
    Abstract: A phenylalanine derivative having the formula (I): ##STR1## wherein A represents ##STR2## B represents ##STR3## wherein m is 0, 1, or 2 and n is 3, 4, or 5; X represents (a) hydroxy, (b) nitro, (c) amino, (d) phenoxy which may be substituted with (i) halogen or (ii) nitro, (e) c.sub.1 -C.sub.4 alkyloxy which may be substituted wit (i) phenyl or (ii) benzoyl, (f) benzoyl, (g) pyridyloxy which may be substituted with (i) halogen or (ii) nitro, or (h) c.sub.1 -C.sub.4 alkyl which may by substituted with halogen;Y represents ##STR4## or --OR.sup.3 wherein R.sup.1 R.sup.2 are independently (a) hydrogen, (b) phenyl which may be substituted with (i) benzoyl, (ii) C.sub.1 -C.sub.4 alkylcarbonyl, (iii) C.sub.1 -C.sub.4 alkyl which may be further substituted with C.sub.1 -C.sub.4 alkoxycarbonyl or hydroxycarbonyl, (iv) C.sub.2 -C.sub.5 alkenyl which may be further substituted with hydroxycarbonyl or C.sub.1 -C.sub.4 alkoxycarbonyl, (v) C.sub.1 -C.sub.
    Type: Grant
    Filed: March 30, 1987
    Date of Patent: October 10, 1989
    Assignees: Shosuke Okamoto, Showa Denko Kabushiki Kaisha
    Inventors: Shosuke Okamoto, Yoshio Okada, Akiko Okunomiya, Taketoshi Naito, Yoshio Kimura, Morihiko Yamada, Norio Ohno, Yasuhiro Katsuura, Hiroshi Nojima, Takashi Shishikura
  • Patent number: 4871870
    Abstract: A compound having the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein A is an amino acid identifying group; B is a hydrogen atom, an alkyl group having 1-5, inclusive, carbon atoms, or an aralkyl group having 6-12, inclusive, carbon atoms; carbon atom 2 is of the R configuration; and carbon atom 3 is of the R configuration. The compounds of the invention are effective in augmenting immunological responses and are useful therefore in the treatment of diseases such as cancer, viral infections, bacterial infections, and arthritis.
    Type: Grant
    Filed: March 16, 1987
    Date of Patent: October 3, 1989
    Assignee: Biomeasure, Inc.
    Inventor: Sun H. Kim
  • Patent number: 4861798
    Abstract: Compounds of the formulae ##STR1## wherein n=6-11, M is hydrogen or a pharmaceutically acceptable cation, R is hydrogen or C.sub.1 -C.sub.6 alkyl optionally substituted by a carboxyl group and X.sub.a, X.sub.b and X.sub.c each independently represent hydrogen or a variety of substituent groups are potent inhibitors of 5-lipoxygenase.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: August 29, 1989
    Assignee: Bristol-Myers Company
    Inventors: Kenneth M. Tramposch, Fred C. Zusi, Suresh A. Marathe
  • Patent number: 4822818
    Abstract: New bicyclic compounds, inclusive of salts thereof, of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each represents hydrogen, hydroxyl or lower alkoxy, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is hydrogen, lower alkyl, amino-lower-alkyl or acylamino-lower-alkyl, R.sup.5 is hydrogen, lower alkyl or aralkyl which may be substituted, R.sup.6 is hydroxyl, lower alkoxy, amino or lower alkylamino, and m and n each means 1 or 2, have inhibitory activities of angiotensin converting enzyme and bradykinin decomposing enzyme, and are useful as antihypertensive agents.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: April 18, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshikazu Oka, Kohei Nishikawa, Akio Miyake
  • Patent number: 4789758
    Abstract: A process is described for the synthesis of N-protected-L-.alpha.-aspartyl-L-phenylalanine by both (a) the rection of an N-protected-L-aspartic anhydride and a R.sub.1 -L-phenylalanine, and (b) the reaction of an N-protected-L-aspartic anhydride and L-phenylalanine in an aqueous medium in the presence of R.sub.2, where R.sub.1 may be an alkali metal salt, alkaline earth metal salt, ammonium salt or organic amine salt, and R.sub.2 may be an ammonium salt or an alkali or alkaline earth metal salt of an inorganic or organic acid.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: December 6, 1988
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tadashi Takemoto, Toshihide Yukawa, Kunio Hisamitsu
  • Patent number: 4786754
    Abstract: A stable, non-hygroscopic, crystalline .gamma.-form of bestatin is prepared from the .alpha.- or .beta.-form of bestatin by heating at a temperature of from about 148.degree. C. to the melting point of bestatin, or by suspending or kneading in certan specified solvents.
    Type: Grant
    Filed: July 13, 1987
    Date of Patent: November 22, 1988
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Hai
    Inventors: Takashi Terada, Tetsushi Saino, Terukatsu Sakurai, Hamao Umezawa, Masaaki Ishizuka
  • Patent number: 4769490
    Abstract: A stable, non-hygroscopic, crystalline .gamma.-form of bestatin is prepared from the .alpha.- or .beta.-form of bestatin by heating at a temperature of from about 148.degree. C. to the melting point of bestatin, or by suspending or kneading in certain specified solvents.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: September 6, 1988
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Takashi Terada, Tetsushi Saino, Terukatsu Sakurai, Hamao Umezawa, Masaaki Ishizuka
  • Patent number: 4743691
    Abstract: 2-(Fluoromethyl or chloromethyl)-2,5-diaminopentanoic acid, 2-(fluoromethyl or chloromethyl)-2,6-diaminohexanoic acid, and 2-fluoromethyl-2-amino-5-guanidinopentanoic acid, and certain derivatives thereof, are inhibitors of ornithine decarboxylase. Methods of preparing the compounds and derivatives are also described.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: May 10, 1988
    Assignee: Merrell Dow France et Cie
    Inventors: Philippe Bey, Michel Jung
  • Patent number: 4743614
    Abstract: Novel compounds of the following formula have restorative pharmacological activities in immuno-deficient hosts, ##STR1## wherein R.sup.1 is amino or a protected amino group,R.sup.2 is hydrogen, carboxy or a protected carboxy group,R.sup.3 is hydrogen, carboxy or a protected carboxy group,R.sup.4 is lower alkyl, amino(lower)alkyl, protected amino(lower)alkyl, carbamoyl(lower)alkyl or protected carbamoyl(lower)alkyl,R.sup.5 is hydrogen or lower alkyl, andR.sup.6 is hydrogen, hydroxyphenyl(lower)alkyl, imidazolyl(lower)alkyl or indolyl(lower)alkyl.
    Type: Grant
    Filed: March 4, 1986
    Date of Patent: May 10, 1988
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Terano, Yasuhisa Tsurumi, Hiroyuki Setoi, Masashi Hashimoto, Masanobu Kohsaka
  • Patent number: 4740616
    Abstract: A process is described for the synthesis of N-protected-L-.alpha.-aspartyl-L-phenylalanine by both (a) the reaction of an N-protected-L-aspartic anhydride and a R.sub.1 -L-phenylalanine, and (b) the reaction of an N-protected-L-aspartic anhydride and L-phenylalanine in an aqueous medium in the presence of R.sub.2, where R.sub.1 may be an alkali metal salt, alkaline earth metal salt, ammonium salt or organic amine salt, and R.sub.2 may be an ammonium salt or an alkali or alkaline earth metal salt of an inorganic or organic acid.
    Type: Grant
    Filed: July 1, 1986
    Date of Patent: April 26, 1988
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tadashi Takemoto, Toshihide Yukawa, Kunio Hisamitsu
  • Patent number: 4735959
    Abstract: There are described novel carboxylic acid derivatives of the formula ##STR1## and derivatives of the formula ##STR2## and the addition salts thereof, which exhibit an effect on the intermediary metabolism. Furthermore, the compounds of Formula Ia as well as the compounds of Formula I possess blood-sugar lowering properties.
    Type: Grant
    Filed: May 14, 1985
    Date of Patent: April 5, 1988
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Wolfgang Grell, Gerhart Griss, Robert Sauter, Rudolf Hurnaus, Eckhard Rupprecht, Nikolaus Kaubisch, Joachim Kahling, Bernhard Eisele
  • Patent number: 4717736
    Abstract: Compounds having the formula: ##STR1##are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory agents and cytoprotective agents.
    Type: Grant
    Filed: November 21, 1984
    Date of Patent: January 5, 1988
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Joshua Rokach, Robert N. Young
  • Patent number: 4695580
    Abstract: Novel phenylserine derivatives of the formula: ##STR1## and pharmaceutically acceptable acid addition salts thereof, pharmaceutical compositions, and a process for preparing the compounds are disclosed. The phenylserine derivatives and pharmaceutically acceptable acid addition salts are capable of inhibiting the biosynthesis of leucotrienes and/or antagonistic activity against SRS-A and hence are useful for prophylaxis and treatment of various allergic diseases (e.g. bronchial asthma, allergic nasitis, urticaria), ischemic heart diseases, ischemic encephalopathy, inflammation, or the like.
    Type: Grant
    Filed: December 19, 1984
    Date of Patent: September 22, 1987
    Assignee: Sumitomo Pharmaceuticals Company, Ltd.
    Inventors: Naohito Ohashi, Shoji Nagata, Masashi Nakatsuka, Kikuo Ishizumi, Junki Katsube, Shunji Aono, Teruo Sakurama
  • Patent number: 4670572
    Abstract: There are described stable fluorescent labels comprising a complex of lanthanide metal and a chelating agent comprising a nucleus which is a triplet sensitizer having a triplet energy greater than that of said lanthanide metal and at least two heteroatom-containing groups which form coordinate complexes with lanthanide metals and a third heteroatom-containing group or heteratom in or appended to the triplet sensitizer. Labeled physiologically active materials useful in specific binding assays such as labeled antigens, heptens, antibodies, hormones and the like comprising the stable fluorescent labels having physiologically active materials adsorbed or bonded thereto are also described.
    Type: Grant
    Filed: February 3, 1986
    Date of Patent: June 2, 1987
    Assignee: Eastman Kodak Company
    Inventors: Jerald C. Hinshaw, John L. Toner, George A. Reynolds
  • Patent number: 4668703
    Abstract: This invention is for .gamma.-allenyl-.gamma.-aminobutyric acid derivatives which are .gamma.-aminobutyric acid transaminase inhibitors.
    Type: Grant
    Filed: July 1, 1985
    Date of Patent: May 26, 1987
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Alexander Krantz, Arlindo L. Castelhano, Diana H. Pliura
  • Patent number: 4668727
    Abstract: Ester substituted benzylhydroxylamine derivatives are effective in stabilizing polyolefin compositions containing a stabilizer or mixture of stabilizers selected from the group consisting of the phenolic antioxidants, the hindered amine light stabilizers, the alkylated hydroxybenzoate light stabilizers, the ultraviolet light absorbers, the organic phosphorus compounds, the alkaline metal salts of fatty acids and the thiosynergists, against degradation upon high temperature extrusion, exposure to the combustion products of natural gas, gamma irradiation or upon storage for extended periods. These ester substituted benzylhydroxylamine derivatives exhibit resistance to loss or extraction during processing and in end-use applications.
    Type: Grant
    Filed: November 21, 1985
    Date of Patent: May 26, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Ramanathan Ravichandran, Thomas E. Snead
  • Patent number: 4661606
    Abstract: Amino acids can be purified and/or concentrated by extracting aqueous mixtures such as fermentation broths by contacting an aqueous mixture containing amino acids with an organic solution containing a water insoluble extractant.
    Type: Grant
    Filed: June 6, 1984
    Date of Patent: April 28, 1987
    Assignee: Henkel Corporation
    Inventors: Francis W. Tuominen, Ronald R. Swanson, Phillip L. Mattison, Kenneth D. MacKay, Bradley W. Glorvigen
  • Patent number: 4639468
    Abstract: A glycinamide derivative of the general formula I: ##STR1## wherein: R is a linear or ramified alkyl group C.sub.5 -C.sub.18, a linear or ramified alkenyl group C.sub.5, C.sub.6, C.sub.7, C.sub.8, C.sub.9, C.sub.10, C.sub.11, C.sub.12, C.sub.13, C.sub.14, C.sub.15, C.sub.16, C.sub.17 or C.sub.18, a linear or ramified alkynyl group C.sub.4 -C.sub.10, a linear or ramified acyl group C.sub.4 -C.sub.18, a linear or ramified alkyl group C.sub.1 -C.sub.10, substituted by a phenoxy group, by a hydroxy radical, by an acetoxy radical, by a carboxy radical, by a linear or ramified alkoxycarbonyl group C.sub.1 -C.sub.4, by a carbonyl radical, by a carboxaldehyde group, by an acetal or cetal group, by one or more phenyl groups, by one or more phenyl groups substituted by a halogen atom such as fluorine, chlorine or bromine,R.sub.1 represents hydrogen, a linear or ramified alkyl group C.sub.1, C.sub.2, C.sub.3, C.sub.4, C.sub.5, C.sub.6, C.sub.7, C.sub.8, C.sub.9 or C.sub.10, a linear or ramified acyl group C.sub.1 -C.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: January 27, 1987
    Assignee: Continental Pharma Inc.
    Inventors: Romeo Roncucci, Claude L. Gillet, Alexis H. Cordi, Mark A. Martens, Joseph L. Roba, Paul J. Niebes, Georges E. Lambelin, William R. Van Dorsser
  • Patent number: 4629736
    Abstract: Fatty acid derivatives represented by the general formula ##STR1## and salts thereof. The compounds of this invention have excellent fibrinolytic action and a highly improved solubility.
    Type: Grant
    Filed: September 28, 1984
    Date of Patent: December 16, 1986
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Shin-ichi Tsukamoto, Yoshinobu Nagano, Kimio Katsuda
  • Patent number: 4622420
    Abstract: A simple method for making EDTA, ED3A or DTPA analogs from amide derivatives of alpha amino acids is disclosed. These EDTA, ED3A or DTPA analogs are useful chelating agents, and preferably are useful as bifunctional chelating agents which may be attached to biological molecules and which form physiologically stable chelates with a variety of metal ions.
    Type: Grant
    Filed: February 5, 1985
    Date of Patent: November 11, 1986
    Assignee: The Regents of the University of California
    Inventors: Claude F. Meares, Simon M. Yeh, David G. Sherman
  • Patent number: 4618708
    Abstract: Derivatives having the general formula: ##STR1## in which the various radicals A,B,X,R.sub.1, R.sub.2, R.sub.3 and n have indicated definitions. These compounds have in particular enkephalinase-inhibiting, antalgic, antidepressive, antidiarrhea and hypotensive activities.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: October 21, 1986
    Inventors: Bernard Roques, Jean-Charles Schwartz, Jeanne-Marie Lecomte
  • Patent number: 4596800
    Abstract: A compound of formula (I) ##STR1## or a pharmaceutically acceptable salt thereof, in which R.sup.1 is hydrogen, halogen, or trifluoromethyl;R.sup.2 is hydrogen or halogen;R.sup.3 is hydrogen or methyl;R.sup.4 is --O(CH.sub.2).sub.a CO.sub.2 H or an ester or amide derivative thereof, O(CH.sub.2).sub.b M or --CO.sub.2 H or an ester or amide derivative thereofwhereina is an integer from 1 to 6,b is an integer from 2 to 7, andM is hydroxy, C.sub.1-6 alkoxy or ##STR2## wherein R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-6 alkyl or ##STR3## together form a five or six membered ring; R.sup.5 is C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted by carboxy or esters and amides thereof; or phenyl optionally substituted by C.sub.1-6 alkyl, halogen, alkoxy or trifluoromethyl;R.sup.8 is hydrogen or C.sub.1-6 alkyl or R.sup.8 together withR.sup.5 form a carbocyclic ring; andn is 1 or 2.Processes for preparing these compounds and their use in therapy is also described.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: June 24, 1986
    Assignee: Beecham Group p.l.c.
    Inventors: Anthony T. Ainsworth, Richard M. Hindley
  • Patent number: 4588836
    Abstract: A compound of the formula ##STR1## wherein R is L-leucyl or .gamma.-L-glutamyl and X and Y are halogen and are the same or different, or a salt thereof. These compounds are useful as synthetic substrates for assaying peptidase activity.
    Type: Grant
    Filed: August 24, 1983
    Date of Patent: May 13, 1986
    Assignees: Toyo Jozo Kabushiki Kaisha, Kokusan Chemical Works Limited
    Inventors: Kunio Matsumoto, Yoshitaka Kagimoto, Tsutomu Hirata, Susumu Watanabe, Akira Ohtsuka, Kiyoharu Takahashi
  • Patent number: 4571345
    Abstract: Compounds of the formula: ##STR1## wherein n is 0 or 1, R is lower alkyl (substituted or unsubstituted), R' is H or lower alkyl, and R" is a branched alkyl, alkyl-cycloalkyl, cycloalkyl, polycycloalkyl (poly=2 or more, fused or non-fused), phenyl or alkyl-substituted phenyl, and physiologically acceptable cationic and acid addition salts thereof, which compounds are potent sweeteners. These derivatives of gem-diaminoalkanes are many times sweeter than sugar and are free from undesirable flavor qualities. Furthermore, they possess an unanticipated high degree of solubility compared with known synthetic sweeteners. In addition, the compounds possess high stability so that they can be used in all types of beverages and in conventional food processing. Sweetening compositions and sweetened edible compositions of these compounds are also provided.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: February 18, 1986
    Assignee: Cumberland Packing Corp.
    Inventors: Michael S. Verlander, William D. Fuller, Murray Goodman
  • Patent number: 4560795
    Abstract: Novel halomethyl derivatives of .alpha.-amino acids of the following general structure: ##STR1## wherein Y is F.sub.2 CH--, F.sub.3 C--, Cl.sub.2 CH--; Z is .beta.-methylthioethyl, .beta.-thioethyl, .beta.-benzylthioethyl; S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, R.sub.a HN(CH.sub.2).sub.n -- wherein n is the integer 3 or 4 or ##STR2## wherein Y.sub.2 is F.sub.2 CH--, or F.sub.3 C--; each of R.sub.a and R.sub.b can be the same or different and is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or ##STR3## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.
    Type: Grant
    Filed: February 6, 1984
    Date of Patent: December 24, 1985
    Assignee: Merrell Dow France et Cie.
    Inventors: Philippe Bey, Michel Jung
  • Patent number: 4528397
    Abstract: An aminocarboxylic acid derivative represented by the formula ##STR1## wherein R.sub.1 and R.sub.2, independently from each other, represent a hydrogen atom or an alkyl group which may have a substituent, and Y represents --NH-- or --S--, provided that when Y represents --NH--, at least one of R.sub.1 and R.sub.2 represents an alkyl group which may have a substituent. These compounds have excellent inhibitory activity on dipeptidase in animals, and are useful for administration in combination with carbapenem antibiotics.
    Type: Grant
    Filed: March 29, 1983
    Date of Patent: July 9, 1985
    Assignee: Sanraku-Ocean Co., Ltd.
    Inventors: Norio Shibamoto, Takeo Yoshioka, Yasuo Fukagawa, Tomoyuki Ishikura
  • Patent number: 4504492
    Abstract: Compounds of the general formula ##STR1## wherein Ph is a phenyl group which is optionally substituted by one or more substituents selected from halo (i.e. fluoro, chloro, bromo or iodo), C.sub.1-4 alkyl, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino, nitro, sulphonyl, aminosulphonyl, trihalomethyl, carboxy, C.sub.1-4 alkoxycarbonyl, amido, C.sub.1-4 alkylamido, C.sub.1-4 alkoxy, C.sub.2-4 alkenyl, cyano, aminomethyl, or methylsulphonyl; Y is a group of formula ##STR2## where R.sup.1 is hydrogen or methyl; R.sup.2 is alkyl of 1 to 3 carbon atoms or is methylthiomethyl; and Z is --OR.sup.3 or --NR.sup.4 R.sup.5 where R.sup.3, R.sup.4 and R.sup.5 are each hydrogen or alkyl of 1 to 4 carbon atoms and R.sup.3 can further be phenylalkyl having 1 to 3 carbon atoms in the alkylene moiety thereof, or phenyl; and basic salts thereof. These compounds have an advantageous enkephalinase inhibitory activity which renders the compounds useful in medical therapy, e.g.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: March 12, 1985
    Assignee: Burroughs Wellcome Co.
    Inventors: Samuel Wilkinson, George W. Hardy
  • Patent number: 4489008
    Abstract: Hydrolytically stable hydroxyl-terminated liquid polymers that are useful in the preparation of polyurethanes prepared by reacting at least one aminoalcohol with a carboxyl-terminated liquid polymer having a carbon-carbon backbone. The hydroxyl-terminated polymers have the formula ##STR1## wherein B is a carbon-carbon backbone, X is HO-- or HO--Y-- a univalent radical obtained by removing a hydrogen atom from an amine group of aminoalcohol containing one primary or secondary hydroxyl group and one primary or secondary amine group per molecule, and the polymers contain an average of greater than 1.5 terminal hydroxyl groups per molecule.
    Type: Grant
    Filed: August 9, 1982
    Date of Patent: December 18, 1984
    Assignee: The B. F. Goodrich Company
    Inventor: Changkiu K. Riew
  • Patent number: 4474764
    Abstract: New 3-N-acyl derivatives of 3-amino-2-hydroxy-4-phenylbutanoic acid are provided, which exhibit analgesic activity and are affective to enhance the morphine analgesia.
    Type: Grant
    Filed: September 28, 1982
    Date of Patent: October 2, 1984
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Hamao Umezawa, Tomio Takeuchi, Takaaki Aoyagi, Mitsugu Hachisu, Kenji Kawamura, Shunzo Fukatsu, Yasuharu Sekizawa
  • Patent number: 4452783
    Abstract: Aminoacid and peptide derivatives of the formula:A--NH--R.sub.1 --CO].sub.x [NH--R.sub.2 --CO].sub.y NH--R.sub.4 --COOHin which A, R.sub.1, R.sub.2, x and y have the meanings specified in claim 1 for formula I, and R4 is a residue of an .alpha.-aminoacid which, when A is 4-allyloxy-3-chloro-phenylacetyl and x and y are 0, contains at least 2 carbon atoms, and their physiologically acceptable salts and lower alkyl ester.These compounds and 4-allyloxy-3-chloro-phenylacetylglycine have anti-inflammatory activity and pharmaceutical compositions containing them are described.
    Type: Grant
    Filed: April 21, 1982
    Date of Patent: June 5, 1984
    Inventors: Robert E. Marks, James S. Burton, John A. Elvidge, Saresh Shah
  • Patent number: 4453003
    Abstract: A process for producing threo-3-amino-2-hydroxybutanoylaminoacetic acids comprises the steps of allowing to react a starting compound represented by the general formula: ##STR1## wherein R.sub.1 represents a naphthyl or a group of the formula: ##STR2## in which R.sub.6 and R.sub.7 represent individually hydrogen, halogen, amino or a protected amino, hydroxy or a protected hydroxy, a lower alkoxy or a lower alkyl and R.sub.2 represents a protected amino, with a starting compound represented by the general formula: ##STR3## wherein R.sub.3 represents hydrogen or an ester residue, to obtain threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its ester represented by the general formula: ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 have the same meanings as above, and then reducing the same into threo-3-protected amino-2-hydroxybutanoic acid or its ester represented by the general formula: ##STR5## wherein R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: December 31, 1981
    Date of Patent: June 5, 1984
    Inventors: Hamao Umezawa, Takaaki Aoyagi, Tadashi Shirai, Rinzo Nishizawa, Masao Suzuki, Tetsushi Saino
  • Patent number: 4439619
    Abstract: Fluorinated alkenylene diamine compounds are inhibitors of ornithine decarboxylase enzyme in vivo and have the following formula: ##STR1## wherein: R.sub.a represents hydrogen or R.sub.2, where R.sub.2 is as defined below;R.sub.b represents hydrogen or, when R.sub.a is hydrogen, R.sub.2, where R.sub.2 is as defined below;R.sub.c represents hydrogen or --COR.sub.3, where R.sub.3 is as defined below;R.sub.1 represents hydrogen or C.sub.1 --C.sub.6 alkyl;each R.sub.2, independently, represents C.sub.2 -C.sub.5 alkylcarbonyl, phenylcarbonyl, phenyl-(C.sub.1 -C.sub.4 alkyl) carbonyl, or an aminocarboxylic acid residue derived by removal of an hydroxy group from a carboxy moiety of an L-aminocarboxylic acid;R.sub.3 represents hydroxy, or, when R.sub.a and R.sub.b are both hydrogen, C.sub.1 -C.sub.8 alkoxy, --NR.sub.4 R.sub.5, where R.sub.4 and R.sub.5 are as defined below, or an aminocarboxylic acid residue derived by removal of an hydrogen atom from the amino moiety of an L-aminocarboxylic acid;R.sub.4 and R.sub.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: March 27, 1984
    Assignee: Merrell Toraude et Compagnie
    Inventors: Philippe Bey, Fritz Gerhart, Michel Jung
  • Patent number: 4432907
    Abstract: Species-linked diamine triacetic acids of the formula ##STR1## wherein T is an organic species containing at least one amine, hydroxyl, or thio functional group, L is the residue of at least one of those functional groups and R is a two or more atom long covalent bridge, are disclosed. Methods for their preparation, for the preparation of metal chelates from them and for the use of the chelates are also disclosed. In a preferred embodiment, the metal ions employed in the formation of the chelates are rare earth metal ions capable of forming fluorescent chelates which can in turn be employed in fluoroassay techniques.
    Type: Grant
    Filed: May 5, 1981
    Date of Patent: February 21, 1984
    Assignee: Analytical Radiation Corporation
    Inventors: Irwin Wieder, Robert H. Wollenberg
  • Patent number: 4421765
    Abstract: Phenylacetic acid amide compounds of the formula ##STR1## in which R.sub.1 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.2 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.3 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35 and R.sub.4 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35, and in which R.sub.5 is a radical of aliphatic character containing the group R.sub.6, R.sub.6 and R.sub.7 are each hydrogen or together are a divalent aliphatic radical and the group of the formula --C(.dbd.O)--R.sub.8 (Ia) is a carboxyl group, which can be functionally modified, and their salts are useful as anti-inflammatory agents.
    Type: Grant
    Filed: October 3, 1980
    Date of Patent: December 20, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Sallmann, Gerhard Baschang
  • Patent number: 4420490
    Abstract: Phenylacetic acid amide compounds of the formula ##STR1## in which R.sub.1 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.2 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.3 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35 and R.sub.4 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35, and in which R.sub.5 is a radical of aliphatic character containing the group R.sub.6, R.sub.6 and R.sub.7 are each hydrogen or together are a divalent aliphatic radical and the group of the formula --C(.dbd.O)--R.sub.8 (Ia) is a carboxyl group, which can be functionally modified, and their salts are useful as anti-inflammatory agents.
    Type: Grant
    Filed: December 17, 1980
    Date of Patent: December 13, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Sallmann, Gerhard Baschang
  • Patent number: 4418077
    Abstract: Fluorinated aminobutyric acid and diaminobutane compounds in vivo are inhibitors of gamma-aminobutyric acid transaminase and have the following formula: ##STR1## wherein: Y represents hydrogen or fluorine;Z represents --CH.sub.2 NR.sub.1 R.sub.2, where R.sub.1 and R.sub.2 are as defined below, or --COR.sub.3 where R.sub.3 is as defined below;R.sub.a represents hydrogen or R.sub.4, where R.sub.4 is as defined below;R.sub.1 represents hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl-(C.sub.1 -C.sub.4 alkyl);R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl-(C.sub.1 -C.sub.4 alkyl) or, when R.sub.a is hydrogen, R.sub.4, where R.sub.4 is as defined below;R.sub.3 represents hydroxy, or when R.sub.a is hydrogen, C.sub.1 -C.sub.8 alkoxy, --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are as defined below, or an aminocarboxylic acid residue derived by removal of an hydrogen atom from the amino moiety of an L-aminocarboxylic acid;each R.sub.4, independently, represents C.sub.2 -C.sub.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: November 29, 1983
    Assignee: Merrell Toraude et Compagnie
    Inventors: Philippe Bey, Fritz Gerhart, Michel Jung, Daniel Schirlin
  • Patent number: 4409213
    Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.
    Type: Grant
    Filed: November 10, 1982
    Date of Patent: October 11, 1983
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Harry Finch, Roger F. Newton, Christopher J. Wallis
  • Patent number: 4402975
    Abstract: A compound represented by the following formula ##STR1## wherein R.sup.1 represents a hydrogen atom, an acyl group or an alkoxycarbonyl group; X.sup.1 represents an alkylene group having 3 to 6 carbon atoms, a 1,4-cyclohexylene group, or a 1,4-phenylene group, the alkylene group may be substituted by an alkyl group having 1 to 6 carbon atoms, and the 1,4-phenylene group may be substituted by 1 or 2 substituents selected from halogen atoms and alkoxy groups having 1 to 6 carbon atoms; R.sup.2 represents a hydrogen atom or a hydroxyl group and R.sup.3 represents hydrogen atom, or R.sup.2 and R.sup.3 together may form an oxo group (.dbd.O), and when X.sup.1 is other than the 1,4-phenylene group, R.sup.2 represents a hydrogen atom and R.sup.3 represents a bond between the carbon atoms to which R.sup.3 is bonded and that carbon atom of X.sup.1 which is adjacent to said carbon atom; X.sup.
    Type: Grant
    Filed: July 17, 1981
    Date of Patent: September 6, 1983
    Assignee: Teijin Limited
    Inventors: Toru Takeshita, Kenji Hoshina, Akira Ohtsu, Tatsuyuki Naruchi
  • Patent number: 4391986
    Abstract: Threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its esters represented by the formula: ##STR1## wherein R.sub.1 represents naphthyl or a group of the formula ##STR2## in which R.sub.6 and R.sub.7 represent individually hydrogen, halogen, amino, an amino protected with acyl, lower alkyloxycarbonyl or carbamoyl, hydroxy or protected with acyl, lower alkyloxycarbonyl or carbamoyl, lower alkoxy, lower alkyl or phenyl group; R.sub.2 represents an amine protected with acyl, lower alkyloxycarbonyl or carbamoyl; and R.sub.3 represents hydrogen, lower alkyl having 1 to 6 carbon atoms or benzyl.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: July 5, 1983
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hamao Umezawa, Takaaki Aoyagi, Tadashi Shirai, Rinzo Nishizawa, Masao Suzuki, Tetsushi Saino
  • Patent number: 4387244
    Abstract: Alkyl-substituted hydroxy benzyl amino acid oligomers are effective metal chelating agents in a broad range of non-aqueous systems. The products claimed display surprisingly high solubilities in a broad range of substituted and unsubstituted aliphatic and aromatic solvents.
    Type: Grant
    Filed: October 23, 1981
    Date of Patent: June 7, 1983
    Assignee: W. R. Grace & Co.
    Inventors: Patricia M. Scanlon, E. Richard Young
  • Patent number: 4386031
    Abstract: The present invention refers to N-Benzoyl-.omega.
    Type: Grant
    Filed: November 6, 1981
    Date of Patent: May 31, 1983
    Assignee: A. Nattermann & Cie GmbH
    Inventors: Gerd Hilboll, Hans-Heiner Lautenschlager, Brigitte Stoll, Manfred Probst
  • Patent number: 4375477
    Abstract: Beta-monofluoromethyl beta-alanine, beta-difluoromethyl beta-alanine and pharmaceutically acceptable esters and amides derived from the acid group, amides derived from the amine group, and salts thereof are novel compounds which inhibit .gamma.-aminobutyric acid transaminase (GABA-T).
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: March 1, 1983
    Assignee: Merrell Toraude et Compagnie
    Inventors: Philippe Bey, Michael Jung, Fritz Gerhart
  • Patent number: 4359477
    Abstract: Complexes of enterochelin, and certain analogues thereof, with one of the metals indium and scandium are useful for the treatment of bacterial infections.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: November 16, 1982
    Assignee: National Research Development Corporation
    Inventor: Henry J. Rogers
  • Patent number: 4352751
    Abstract: Species-linked diamine triacetic acids of the formula ##STR1## wherein T is an organic species containing at least one amine, hydroxyl, or thiol functional group, L is the residue of at least one of those functional groups and R is a two or more atom long covalent bridge, are disclosed. Methods for their preparation, for the preparation of metal chelates from them and for the use of the chelates are also disclosed. In a preferred embodiment, the metal ions employed in the formation of the chelates are rare earth metal ions capable of forming fluorescent chelates which can in turn be employed in fluoroassay techniques.
    Type: Grant
    Filed: September 10, 1979
    Date of Patent: October 5, 1982
    Assignee: Analytical Radiation Corporation
    Inventors: Irwin Wieder, Robert H. Wollenberg
  • Patent number: 4338460
    Abstract: A process for preparing in high yield an isolable orthohydroxydiaminodicarboxylic acid which is useful as a metal chelating agent. The process comprises reacting a phenol (or mixture of phenols), a diaminodicarboxylic acid (or acid source), and a formaldehyde source in a medium having an acidic pH.
    Type: Grant
    Filed: August 20, 1980
    Date of Patent: July 6, 1982
    Assignee: W. R. Grace & Co.
    Inventors: Roger R. Gaudette, John L. Ohlson, Patricia M. Scanlon
  • Patent number: 4336405
    Abstract: There are described novel compounds which include a silver halide developing function, a colorless ligand which is a radical of an iminodiacetic acid and a radical containing an onium group. The compounds are useful in photography as silver halide developing agents and also may be complexed with metals to form dye developers.
    Type: Grant
    Filed: July 11, 1980
    Date of Patent: June 22, 1982
    Assignee: Polaroid Corporation
    Inventor: Elbert M. Idelson
  • Patent number: 4326071
    Abstract: Novel compounds of the following general formula are useful pharmacological agents: ##STR1## wherein Y is FCH.sub.2 - or F.sub.2 CH-; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, -NR.sub.10 R.sub.11 wherein each of R.sub.10 and R.sub.11 is hydrogen or a straight or branched alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.12 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.2 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR3## wherein R.sub.8 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and n is the integer 2 or 3; pharmaceutically acceptable salts and individual optical isomers thereof.
    Type: Grant
    Filed: September 28, 1977
    Date of Patent: April 20, 1982
    Assignee: Merrell Toraude et Compagnie
    Inventors: Philippe Bey, Michel Jung
  • Patent number: 4323704
    Abstract: Novel compounds of the formula ##STR1## wherein A is methylene, ethylene or ethylidene; R.sub.1 is --C.tbd.CH or --CH.dbd.CH.sub.2 ; R.sub.2 is hydrogen or COR wherein R is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.5 is hydrogen or a straight or branched lower alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.6 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.a is hydrogen, ##STR3## alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR4## wherein R.sub.7 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl and p-hydroxybenzyl; and R.sub.b has the same meaning as defined for R.sub.a except R.sub.b is not ##STR5## and R.sub.a and R.sub.
    Type: Grant
    Filed: January 16, 1981
    Date of Patent: April 6, 1982
    Assignee: Merrell Toraude et Compagnie
    Inventors: Brian W. Metcalf, Michel Jung, Charles Danzin
  • Patent number: 4322436
    Abstract: Phenylacetic acid amide compounds of the formula ##STR1## in which R.sub.1 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.2 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.3 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35 and R.sub.4 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35, and in which R.sub.5 is a radical of aliphatic character containing the group R.sub.6, R.sub.6 and R.sub.7 are each hydrogen or together are a divalent aliphatic radical and the group of the formula --C(.dbd.O)--R.sub.8 (Ia) is a carboxyl group, which can be functionally modified, and their salts are useful as anti-inflammatory agents.
    Type: Grant
    Filed: December 17, 1980
    Date of Patent: March 30, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Sallmann, Gerhard Baschang
  • Patent number: 4281180
    Abstract: A process for producing threo-3-amino-2-hydroxybutanoylaminoacetic acids comprises the steps of allowing to react a starting compound represented by the general formula: ##STR1## wherein R.sub.1 represents a naphthyl or a group of the formula: ##STR2## in which R.sub.6 and R.sub.7 represent individually hydrogen, halogen, amino or a protected amino, hydroxy or a protected hydroxy, a lower alkoxy or a lower alkyl and R.sub.2 represents a protected amino, with a starting compound represented by the general formula: ##STR3## wherein R.sub.3 represents hydrogen or an ester residue, to obtain threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its ester represented by the general formula: ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 have the same meanings as above, and then reducing the same into threo-3-protected amino-2-hydroxybutanoic acid or its ester represented by the general formula: ##STR5## wherein R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: November 23, 1979
    Date of Patent: July 28, 1981
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hamao Umezawa, Takaaki Aoyagi, Tadashi Shirai, Rinzo Nishizawa, Masao Suzuki, Tetsushi Saino