Oxy Patents (Class 562/444)
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Patent number: 5691381Abstract: The present invention provides novel hydroxamic acids and carbocyclic acids and derivatives thereof and to pharmaceutical compositions and methods of use of these novel compounds for the inhibition of matrix metalloproteinases, such as stromelysin, and inhibit the production of tumor necrosis factor alpha, and for the treatment of arthritis and other related inflammatory diseases.Type: GrantFiled: April 16, 1996Date of Patent: November 25, 1997Assignee: The DuPont Merck Pharmaceutical CompanyInventors: Irina Cipora Jacobson, Carl Peter Decicco, Robert Joseph Cherney
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Patent number: 5686423Abstract: A series of di- and tri-peptide mimetic dopamine prodrugs are synthesized in which D-phenylglycine or D-p-hydroxyphenylglycine is attached as tools for delivery of L-dopa through the intestine via the intestinal dipeptide-mediated carrier transport system. These compounds are found useful as an active ingredient for the treatment of Parkinson's disease.Type: GrantFiled: February 16, 1996Date of Patent: November 11, 1997Assignee: Department of Health, the Executive Yuan, Republic of ChinaInventors: Hui-Po Wang, Jia-Shuai Lee, Ming-Cheng Tsai, Hsiao-Hwa Lu, Oliver Yoa-Pu Hu, Wen-Lin Luo
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Patent number: 5686472Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.Type: GrantFiled: October 27, 1993Date of Patent: November 11, 1997Assignee: Merck & Co., Inc.Inventors: Neville J. Anthony, S. Jane deSolms, Ta Jyh Lee, deceased
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Patent number: 5684168Abstract: .beta.-phenylisiserine-(2R,3S), salts and preparation thereof through the action of ammonia on .beta.-phenylglycidic-(2R,3R) acid and its use in the preparation of taxane derivatives of general formula: ##STR1## wherein R is hydrogen or --COCH.sub.3 ;and R.sub.1 is phenyl or --O--C(CH.sub.3).sub.3.Type: GrantFiled: April 10, 1995Date of Patent: November 4, 1997Assignee: Rhone-Poulenc Rorer S.A.Inventors: Jean-Pierre Duchesne, Max Ferraro
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Patent number: 5679711Abstract: The invention concerns the discovery of the surprising and unexpected therapeutic effects of hydroxyl ions. The observed medicinal properties of these ions are both novel and broad in scope. The acute corrosive effects and toxicity of hydroxyl ions on living tissue has previously overwhelmed their therapeutic attributes. Unique hydroxyl ion modulating compounds have been discovered and are within the scope of the invention. When used appropriately as companions with hydroxyl ions, these modulating compounds obviate and attenuate the harmful effects of hydroxyl ions, unmasking and revealing their previously unknown and undemonstratable therapeutic properties. These hydroxyl ion modulating compounds do not significantly interfere with the surprising and unexpected therapeutic benefits of the hydroxyl ions. The novel hydroxyl ion modulating compounds are generally characterized as N,N-disubstituted-aminoalkanoate salts and substituted N,N-substituted-aminoalkanoate salts.Type: GrantFiled: June 7, 1995Date of Patent: October 21, 1997Assignee: FHJ Scientific, Inc.Inventors: Delton R. Carrell, Edward J. Cragoe, Jr.
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Patent number: 5676923Abstract: Diethylenetriaminepentaacetic acid monoamide derivatives, their complexes and complex salts, containing an element of atomic numbers 21-29, 31, 32, 39, 42-44, 49 or 57-83, pharmaceutical agents containing these compounds, their use as contrast media and process for their production.Type: GrantFiled: June 7, 1995Date of Patent: October 14, 1997Assignee: Schering AktiengesellschaftInventors: Johannes Platzek, Ulrich Niedballa, Peter Mareski, Bernd Raduchel, Hanns-Joachim Weinmann, Andreas Muhler, Bernd Misselwitz
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Patent number: 5668112Abstract: Esters or amides of a peptide, preferably a dipeptide, consisting essentially of natural or synthetic L-amino acids with hydrophobic side chains were found to have specific cellular toxicities. Preferable amino acids of the peptide are leucine, phenylalanine valine, isoleucine, alanine, proline, glycine or aspartic acid beta methyl ester. Preferable dipeptides are L leucyl L-leucine, L-leucyl L-phenylalanine, L-valyl L-phenylalanine, L-leucyl L-isoleucine, L-phenylalanyl L-phenylalanine, L-valyl L-leucine, L-leucyl L-alanine, L-valyl L-valine, L-phenylalanyl L leucine, L prolyl L-leucine, L-leucyl L-valine, L-phenylalanyl L-valine, L glycyl L-leucine, L-leucyl L-glycine, glycyl L-phenylalanine and L-aspartyl beta methyl ester L-phenylalanine. Most preferable dipeptides are L-leucyl L-leucine, L-leucyl L-phenylalanine, L-valyl L-phenylalanine, L-phenylalanyl L-leucine, L-leucyl L-isoleucine L-phenylalanyl L-phenylalanine and L-valyl L-leucine.Type: GrantFiled: September 22, 1994Date of Patent: September 16, 1997Assignee: Board of Regents, The University of Texas Sys.Inventors: Peter E. Lipsky, Dwain L. Thiele
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Patent number: 5658944Abstract: The present invention is concerned with compounds of formula (I) ##STR1## wherein Ar is a mono- or bicyclic aromatic group optionally containing one or two heteroatoms independently selected from nitrogen, oxygen and sulphur, said group being optionally substituted by one or more atoms or groups independently selected from halogen, nitro, amino, --NRR.sup.1 where R and R.sup.1 are independently selected from hydrogen, C.sub.1-8 alkyl and C.sub.1-8 alkanoyl, cyano, carboxyalkoxy, alkoxycarbonylalkoxy, C.sub.1-8 alkyl (including cycloalkyl and cycloalkylalkyl), C.sub.1-8 alkoxy (including cycloalkoxy and cycloalkylalkoxy), C.sub.Type: GrantFiled: April 14, 1995Date of Patent: August 19, 1997Assignee: The University of South CarolinaInventors: James Mood Chapman, Jr., Roy Lee Hawke, Karl Witold Franzmann, Kevin Julian O'Connor
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Patent number: 5650386Abstract: Modified amino acid compounds useful for the delivery of active agents are provided. The amino acids, non-alpha-amino acids, have been modified by acylation on the amino group particularly with phenyl or cyclohexyl groups. These groups have a variety of substituents including but not limited to hydroxy, methyl, fluoro, chloro, and the like. The compounds of the invention can be combined with numerous active agents including but not limited to heparin, peptides, and parathyroid hormone, and can then be used for effective administration of the active agent. Administration can be, for example, oral or parenteral.Type: GrantFiled: March 31, 1995Date of Patent: July 22, 1997Assignee: Emisphere Technologies, Inc.Inventors: Andrea Leone-Bay, Koc-Kan Ho, Jeffery Bruce Press
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Patent number: 5643958Abstract: The present invention relates to a compound of the formula (I): ##STR1## wherein Ar.sup.1, Ar.sup.2 and Ar.sup.3 represent an aryl group or a heteroaromatic ring group; A represents a hydrocarbon group which may be substituted; Q represents a group of the formula --(CH.sub.2).sub.m -- (m is an integer of from 1 to 6) or --(CH.sub.2).sub.n --W--(CH.sub.2).sub.p -- (W is an oxygen atom, a sulfur atom, a vinylene group or an ethynylene group; n and p are a integer of from 0 to 3); R.sup.1 represents a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group, a lower alkoxy group, an aryl or heteroaromatic ring group which may be substituted; R.sup.2, R.sup.7 and R.sup.8 represent a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group or a lower alkoxy group; R.sup.3 and R.sup.Type: GrantFiled: March 15, 1996Date of Patent: July 1, 1997Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Yoshikazu Iwasawa, Tetsuya Aoyama, Kumiko Kawakami, Sachie Arai, Toshihiko Satoh, Yoshiaki Monden
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Patent number: 5633281Abstract: Compounds of formula (I), or a salt or prodrug thereof, wherein R.sup.1 represents H, C.sub.1-4 alkyl or CH.sub.2 COOH; R.sup.2 represents H or C.sub.1-4 alkyl, with the proviso that R.sup.1 and R.sup.2 are not both H; R.sup.3 and R.sup.4 each independently rely resent H, C.sub.1-, alkyl. C.sub.2-6 alkenyl C.sub.1-6 alkoxy, halo or trifluoromethyl; A.sup.1, A.sup.2, A.sup.3, and A.sup.4 each independently represent H, C.sub.1-6 alkyl, C.sub.1-6 alkenyl, C.sub.1-6 alkoxy, halo or trifluoromethyl; and A.sup.5 and A.sup.6 each independently represent H or C.sub.Type: GrantFiled: December 8, 1995Date of Patent: May 27, 1997Assignee: Merck Sharp & Dohme Ltd.Inventors: Martin R. Teall, Brian J. Williams
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Patent number: 5627211Abstract: Compounds of formula (I), and salts and prodrugs thereof wherein X, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 are defined herein, are tachykinin receptor antagonists.Type: GrantFiled: March 13, 1995Date of Patent: May 6, 1997Assignee: Merck Sharp & Dohme LimitedInventor: Martin R. Teall
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Patent number: 5616790Abstract: An fluorescent metal-chelating amphiphile having the structure: ##STR1## wherein A is a hydrophobic fluorophore, X and Y are aliphatic hydrocarbons having from 9 to 25 carbon atoms, B is a hydrophilic spacer, C is a metal chelator, and L is either an ether or ester linkage. The fluorescent metal-chelating amphiphile is combined with a matrix lipid to form lipid-based sensors which provide fluorometric detection of metal ions in liquids.Type: GrantFiled: November 18, 1994Date of Patent: April 1, 1997Assignee: California Institute of TechnologyInventors: Frances H. Arnold, Darryl Y. Sasaki, Deborah Shnek, Daniel Pack
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Patent number: 5608102Abstract: This invention relates to a method for preparing .beta.-phenylisoserine and analogues thereof having general formula (I) ##STR1## from an aromatic aldehyde and an .alpha.-methylarylamine-S, and through a lactam of general formula (II) as described herein. The acids of general formula (I) (R.dbd.H) may be used to prepare taxane derivatives having remarkable antitumoral and antileukaemic activity.Type: GrantFiled: September 26, 1994Date of Patent: March 4, 1997Assignee: Rhone-Poulenc Rorer S.A.Inventors: Jean-Dominique Bourzat, Alain Commer.cedilla.on
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Patent number: 5602272Abstract: Reduction and resolution methods for the preparation of compounds useful as intermediates in the preparation of taxanes, and particularly for preparation of desired stereoisomers for use in the formation of the C-13 sidechain of pharmaceutically useful taxanes such as paclitaxel.Type: GrantFiled: June 21, 1994Date of Patent: February 11, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Wen-Sen Li, John K. Thottathil
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Patent number: 5599951Abstract: Amino acid derivatives of formula (Ia) and (Ib) and prodrugs thereof containing a group responsible for chelating the zinc atom of enkephalinase and angiotensin convertase enzymes are disclosed as inhibitors of these enzymes.Type: GrantFiled: April 14, 1995Date of Patent: February 4, 1997Assignee: Societe Civile BioprojetInventors: Jean-Christophe Plaquevent, Denis Danvy, Thierry Monteil, Claude Gros, Jean-Charles Schwartz, Jeanne-Marie LeComte, Helene Greciet, Lucette Duhamel, Pierre Duhamel
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Patent number: 5594106Abstract: Compounds and methods are disclosed that are useful in inhibiting the TNF-.alpha. converting enzyme (TACE) responsible for cleavage of TNF-.alpha. precursor to provide biologically active TNF-.alpha.. The compounds employed in the invention are peptidyl derivatives having active groups capable of inhibiting TACE such as, hydroxamates, thiols, phosphoryls and carboxyls.Type: GrantFiled: August 18, 1994Date of Patent: January 14, 1997Assignee: Immunex CorporationInventors: Roy A. Black, Jeffrey N. Fitzner, Paul R. Sleath
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Patent number: 5587514Abstract: A process for the synthesis of hydroxyethylene dipeptide isosteres from .alpha.-N,N-di(protected)-amino(alkyl or substituted alkyl)methyl ketones that can be efficiently carried out on an industrial scale. The process proceeds with excellent diastereoselectivity and chemical efficiency, and can be used to prepare a wide variety of hydroxyethylene dipeptide isosteres for a variety of uses, including as HIV-1 protease inhibitors and renin inhibitors.Type: GrantFiled: November 8, 1993Date of Patent: December 24, 1996Assignee: Emory UniversityInventors: Dennis C. Liotta, Bharat R. Lagu
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Patent number: 5585391Abstract: The invention concerns the discovery of the surprising and unexpected therapeutic effects of hydroxyl ions. The observed medicinal properties of these ions are both novel and broad in scope. The acute corrosive effects and toxicity of hydroxyl ions on living tissue has previously overwhelmed their therapeutic attributes. Unique hydroxyl ion modulating compounds have been discovered and are within the scope of the invention. When used appropriately as companions with hydroxyl ions, these modulating compounds obviate and attenuate the harmful effects of hydroxyl ions, unmasking and revealing their previously unknown and undemonstratable therapeutic properties. These hydroxyl ion modulating compounds do not significantly interfere with the surprising and unexpected therapeutic benefits of the hydroxyl ions. The novel hydroxyl ion modulating compounds are generally characterized as N,N-disubstituted-aminoacetate salts and substituted N,N-substituted-aminoacetate salts.Type: GrantFiled: October 8, 1993Date of Patent: December 17, 1996Assignee: FHJ Scientific, Inc.Inventors: Delton R. Carrell, Edward J. Cragoe, Jr.
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Patent number: 5581007Abstract: A process for preparing an optically active (2S,3S)-allophenylnorstatin derivative (I) is disclosed, comprising asymmetrically hydrogenating a 4-phenyl-2-halogeno-3-oxobutyric ester (III) in the presence of a ruthenium-phosphine complex to obtain a 4-phenyl-(2S)-halogeno-(3R)-hydroxybutyric ester (IV), epoxidizing the ester (IV) in the presence of a base to obtain a 4-phenyl-(2S,3R)-epoxybutyric ester (V), reacting the ester (V) with a tri(lower alkyl)silylazide or a (lower alkyl)diarylsilylazide in the presence of a Lewis to obtain a (3S)-azido-4-phenyl-(2S)-trisubstituted silyloxybutyric ester (VI), hydrogenolyzing the ester (VI) into a (2S,3S)-allophenylnorstatin derivative (VII), protecting the amino group of the compound (VII), and, if desired, hydrolyzing the compound before or after the amino group protection. Compounds (I) can be obtained at high optical purity safely and in good yield.Type: GrantFiled: March 1, 1996Date of Patent: December 3, 1996Assignee: Takasago International CorporationInventors: Noboru Sayo, Tetsuro Yamasaki, Hidenori Kumobayashi, Yoshifumi Yuasa, Tsukasa Sotoguchi
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Patent number: 5574016Abstract: The present invention concerns glycoprotein IIa/IIIb antagonists and platelet aggregation inhibitors of the formula (I): ##STR1## wherein R.sup.1 is aryl which may have one or more suitable substituent(s),R.sup.2 is carboxy(lower)alkyl or protected carboxy(lower)alkyl,R.sup.3 is carboxy or protected carboxy,A.sup.1 is alkylene which may have one or more suitable substituent(s),A.sup.2 is a group of the formula: ##STR2## (wherein R is lower alkyl), or a group of the formula:--NHCH.sub.2 CH.sub.2 CO--,A.sup.3 is lower alkylene which may have one or more suitable substituent(s),l, m and n are each the same or different an integer of 0 or 1,with proviso that A.sup.2 is not a group of the formula:--NHCH.sub.2 CH.sub.2 CO--,when l is an integer of 0.Type: GrantFiled: May 22, 1995Date of Patent: November 12, 1996Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Hisashi Takasugi, Akito Tanaka, Hiroyoshi Sakai, Takatoshi Ishikawa
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Patent number: 5556864Abstract: Compounds of formula (I): ##STR1## [wherein: R.sup.1 is aryl; R.sup.2 is hydrogen, alkyl, alkoxy, halogen or cyano; R.sup.3 is a group of formula --B--NR.sup.4 R.sup.5, where R.sup.4 and R.sup.5 are independently hydrogen, alkyl or substituted alkyl or R.sup.4 and R.sup.5, together with the nitrogen to which they are attached, form a heterocycle, and B is alkylene or a group of formula --CH.sub.2 CH(OR.sup.6)CH.sub.2 --, where R.sup.6 is hydrogen, alkanoyl, substituted alkanoyl or arylcarbonyl, or a group of formula --D--R.sup.7, where D is a single bond or alkylene and R.sup.7 is a heterocycle; and A is alkylene; and pharmaceutically acceptable salts and esters thereof] are useful for the treatment and prevention of circulatory diseases and psychosis.Type: GrantFiled: January 5, 1995Date of Patent: September 17, 1996Assignee: Sankyo Company, LimitedInventors: Koichi Fujimoto, Naoki Tanaka, Fumitoshi Asai, Tomiyoshi Ito, Hiroyuki Koike
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Patent number: 5538986Abstract: Disclosed are compounds of Formula I: ##STR1## or a pharmaceutically acceptable salt or solvate thereof, wherein: R.sup.3 is alkyl, alkenyl, alkynyl, aryl, alkaryl, aralkyl, cycloalkyl, acyloxymethyl, alkoxy, alkoxymethyl, or alkyl substituted with cycloalkyl;R.sup.4 is H, alkyl, alkenyl, alkoxy, or --OH.Also disclosed are pharmaceutical compositions containing compounds of Formula I, methods for inhibiting tumor necrosis factor-.alpha. and methods for treating septic shock, inflammation, or allergic disease by administering a compound of Formula I.Type: GrantFiled: December 6, 1993Date of Patent: July 23, 1996Assignee: Schering CorporationInventors: Pauline C. Ting, Daniel M. Solomon, Richard J. Friary, Frank J. Villani, John J. Piwinski, Joe F. Lee, Dhiru B. Vashi
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Patent number: 5536750Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.Type: GrantFiled: November 30, 1994Date of Patent: July 16, 1996Assignee: Merck & Co., Inc.Inventors: S. Jane deSolms, Samuel L. Graham
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Patent number: 5514808Abstract: The invention concerns the discovery of the surprising and unexpected therapeutic effects of hydroxyl ions. The observed medicinal properties of these ions are both novel and broad in scope. The acute corrosive effects and toxicity of hydroxyl ions on living tissue has previously overwhelmed their therapeutic attributes. Unique hydroxyl ion modulating compounds have been discovered and are within the scope of the invention. When used appropriately as companions with hydroxyl ions, these modulating compounds obviate and attenuate the harmful effects of hydroxyl ions, unmasking and revealing their previously unknown and undemonstratable therapeutic properties. These hydroxyl ion modulating compounds do not significantly interfere with the surprising and unexpected therapeutic benefits of the hydroxyl ions. The novel hydroxyl ion modulating compounds are generally characterized as N,N-disubstituted-aminoacetate salts and substituted N,N-substituted-aminoacetate salts.Type: GrantFiled: August 25, 1994Date of Patent: May 7, 1996Assignee: FHJ Scientific, IncInventors: Delton R. Carrell, Edward J. Cragoe, Jr.
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Patent number: 5514683Abstract: The compounds of the formula I ##STR1## and their pharmaceutical acceptable salts, which are defined herein, are ligands for cholecystokinin and/or gastrin receptors.Type: GrantFiled: August 9, 1994Date of Patent: May 7, 1996Assignee: James Black Foundation LimitedInventors: Sarkis B. Kalindjian, Caroline M. R. Low, Iain M. McDonald, Robert A. D. Hull, Nigel P. Shankley, Ildiko M. Buck, Katherine I. M. Steel, Jonathan M. R. Davies, David J. Dunstone, Elaine A. Harper, Michael J. Pether, Michael J. Bodkin, Matthew J. Tozer, Martin L. Hudson
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Patent number: 5510507Abstract: A process and catalyst composition are provided for the highly efficient enantioselective hydrogenation of dehydroamino acid derivatives. The catalyst composition comprises rhodium or iridium and a diphosphinite carbohydrate ligand, wherein the phosphorous atoms are attached to aromatic groups substituted with electron-donating substituents. Also provided is a means to selectively produce .alpha. amino acids in either the L or the D form, based upon use of a sugar in the ligand with phosphinites attached in an absolute Right-Left or Left-Right configuration, respectively.Type: GrantFiled: April 24, 1995Date of Patent: April 23, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Timothy A. Ayers, Thaliyil V. Rajanbabu
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Patent number: 5503776Abstract: An N-acylamino acid compound represented by the general formula (1):R--CO--(NH--X--CO).sub.n --OR.sup.1 (1)wherein (NH--X--CO) is an amino acid residue, X in (NX--X--CO) is variable with the kind of amino acid to be used, R--CO is a saturated or an unsaturated fatty acid residue having 6 to 24 carbon atoms, R.sup.1 is hydrogen atom, sodium atom, potassium atom, or methyl group and n is an integer in the range of from 1 to 3, indicating that at least one histidine is contained as a component amino acid is disclosed, which is obtained by causing an N-hydroxysuccinimide ester to react with an amino acid or a peptide.The compound excels in antioxidizing power, emulsifying power, antibacterial power, chelating power, infrared absorbing power, and humidity-retaining power.Type: GrantFiled: December 21, 1994Date of Patent: April 2, 1996Assignees: National Food Research Institute Ministry of Agriculture, Forestry and Fisheries, CCI CorporationInventors: Hironobu Murase, Tsutomu Kunieda, Akihiko Nagao, Junji Terao
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Patent number: 5504212Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.Type: GrantFiled: October 29, 1992Date of Patent: April 2, 1996Assignee: Merck & Co., Inc.Inventors: S. Jane de Solms, Samuel L. Graham, John S. Wai
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Patent number: 5496927Abstract: This invention relates to analogs of peptidase substrates in which the amide group containing the scissile amide bond of the substrate peptide has been replaced by an activated electrophilic ketone moiety. These analogs of the peptidase substrates provide specific enzyme inhibitors for a variety of proteases, the inhibition of which will have useful physiological consequences in a variety of disease states.Type: GrantFiled: May 25, 1994Date of Patent: March 5, 1996Assignee: Merrell Pharmaceuticals Inc.Inventors: H. Michael Kolb, Joseph P. Burkhart, Michel J. Jung, Fritz E. Gerhart, deceased, Eugene L. Giroux, Bernhard Neises, Daniel G. Schirlin
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Patent number: 5495044Abstract: The present invention provides inhibitors of kynureninase having the formula ##STR1## where X is CO or CHOH; R.sub.A and R.sub.B, independently of one another, are H, a halogen, a halovinyl group, or a small alkyl or haloalkyl group having one to three carbon atoms; A is a H or an acetyl group; R.sub.1 is H, NH.sub.2, NR.sub.6 R.sub.7, NO.sub.2, halogen, CF.sub.3 or a small alkyl group having from one to three carbon atoms, wherein: R.sub.6 and R.sub.7, independently of one another, are H, a formyl group or a small alkyl group having from one to three carbon atoms with the exception that only one of R.sub.6 or R.sub.7 can be a formyl group; R.sub.2 is OH, H, halogen, CF.sub.3 or a small alkyl group having from one to three carbon atoms; and R.sub.3, R.sub.4 and R.sub.5, independently of one another, are H, halogen, CF.sub.3, NO.sub.2, NH.sub.2, or small alkyl group having from one to three carbon atoms, and with the proviso that when X=CO, neither R.sub.A nor R.sub.B can be CF.sub.3.Type: GrantFiled: October 29, 1993Date of Patent: February 27, 1996Assignee: University of Georgia Research Foundation, Inc.Inventors: Robert S. Phillips, Lakshmi V. Cyr
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Patent number: 5488132Abstract: The invention includes selected novel optically active .alpha.-amino ketones which either are themselves useful or are intermediates for the preparation of known ketomethylene pseudopeptides useful as antibiotics, antibiotic enhancers, or enzyme inhibitors. Further, the present invention provides a method for dehydrogenation/asymmetrical hydrogenation to obtain essentially pure antipodes of ketomethylene pseudopeptides having two chiral centers.Type: GrantFiled: April 22, 1994Date of Patent: January 30, 1996Assignee: Monsanto CompanyInventor: John J. Talley
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Patent number: 5488149Abstract: A compound of the formula (I) or its pharmaceutically acceptable salt or ester: ##STR1## wherein each of the substituents are herein defined.Type: GrantFiled: June 6, 1995Date of Patent: January 30, 1996Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Takashi Nomoto, Masahiro Hayashi, Jun Shibata, Yoshikazu Iwasawa, Morihiro Mitsuya, Yoshiaki Iida, Katsumasa Nonoshita, Yasufumi Nagata
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Patent number: 5482942Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.Type: GrantFiled: June 28, 1994Date of Patent: January 9, 1996Assignee: American Home Products CorporationInventors: Richard M. Soll, Paul J. Dollings
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Patent number: 5476874Abstract: Oligopeptide analogs containing sulfonamide, urea or carbamate linkages in the backbone are described. These compounds are useful in the inhibition of HIV protease, the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.Type: GrantFiled: June 22, 1994Date of Patent: December 19, 1995Assignee: Merck & Co., Inc.Inventors: Randall W. Hungate, Joseph P. Vacca
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Patent number: 5463116Abstract: Stable crystals of N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine may be produced by treating this compound with a solvent at a temperature of at least 10.degree. C. and forming crystals in the solvent at a temperature of at least 10.degree. C. For example, crystals may be formed by crystallization out of solution, or may be formed from solid particles of the compound suspended in a solvent. Crystals formed in this way have different melting point, infra red spectrum and X-ray diffraction patterns from previously known forms of the compound and have enhanced processability, e.g., stability to grinding.Type: GrantFiled: February 2, 1994Date of Patent: October 31, 1995Assignee: Ajinomoto Co., Inc.Inventors: Michito Sumikawa, Yoshihito Koguchi, Takao Ohgane, Yasuo Irie, Satoji Takahashi
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Patent number: 5461045Abstract: A fused benzeneoxyacetic acid derivative of the formula: ##STR1## wherein ##STR2## is (i) ##STR3## (ii) ##STR4## (iii) ##STR5## or (iv) ##STR6## A is (i) ##STR7## or (ii) ##STR8## R.sup.1 is hydrogen or C.sub.1-4 alkyl; R.sup.2 is hydrogen, C.sub.1-6 alkyl or phenyl;R.sup.3 is(i) C.sub.1-15 alkyl,(ii) C.sub.1-8 alkyl substituted by one or two of benzene, C.sub.4-7 cycloalkane or 4-7 ring-membered monocyclic ring which contains one nitrogen atom or(iii) C.sub.10-15 condensed tricyclic ring;e is 3-5;f is 1-3;p is 0-4;q is 0-2;s is 0-3With the proviso that, ring(s) in R.sup.3 may be substituted by one to three of C.sub.1-4 alkyl, .sub.1-4 alkoxy, halogen atom, nitro or trihalomethyl. And, when D--B is the formula (iii) or (iv), --(CH2)p- or .dbd.CH--(CH2)s- is attached at the position of a or b on the ring.Type: GrantFiled: July 14, 1992Date of Patent: October 24, 1995Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Nobuyuki Hamanaka, Kanji Takahashi, Hidekado Tokumoto
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Patent number: 5455230Abstract: Compounds of the formula I as well as a process for their preparation, their pharmaceutical preparations and their useH--Tyr--Tic--X (I)wherein X is--Phe--OH,--Phe--NH.sub.2,--Phe--Phe--OH,--Phe--Phe--NH.sub.2,--Trp--Phe--NH.sub.2,--Trp--Phe--OH,--Phe--Phe(p-NO.sub.2)--OH,--Trp--Phe(p-NO.sub.2)--H or--Phe--Trp--NH.sub.2.Type: GrantFiled: February 24, 1993Date of Patent: October 3, 1995Assignee: Aktiebolaget AstraInventor: Peter W. Schiller
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Patent number: 5436343Abstract: Compounds of formula (I): ##STR1## in which: R.sub.1 and R.sub.2, which may be identical or different, represent a linear or branched (C.sub.1 C.sub.6) alkyl radical, a substituted or unsubstituted phenyl radical, a pyridyl radical or a thienyl radical, or, with the carbon atom to which they are attached, a substituted or unsubstituted (C.sub.4 -C.sub.7) cycloalkyl ring,R.sub.3 representsa substituted or unsubstituted phenylsulfonyl radical,a linear or branched (C.sub.1 -C.sub.6) alkyl radical,an alkylaminocarbonyl radical,or a linear or branched (C.sub.1 -C.sub.6) acyl radical,R.sub.4 represents any one of the radicals:--CH.dbd.CH--(CH.sub.2).sub.p --CO.sub.2 H or --CH.sub.2 --CH.sub.2 --(CH.sub.2)p--CO.sub.2 Hin which p is equal to 0, 1, 2 or 3, n and m, which may be identical or different, represent 0, 1 or 2,their isomers, enantiomers, diastereoisomers and epimers as well as their addition salts with a pharmaceutically acceptable acid or base.Type: GrantFiled: May 14, 1993Date of Patent: July 25, 1995Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Patrick Hautefaye, Michel Laubie, Tony Verbeuren
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Patent number: 5428162Abstract: Novel compounds of the formula (1), ##STR1## in which R.sub.1 is hydrogen or acyl, R.sub.2 to R.sub.5 are independently hydrogen, chloro, alkyl phenylalkyl, aryl, cycloalkyl, alkoxy, alkylthio, hydroxy, amino or substituted amino, R.sub.6 is hydrogen, R.sub.7 to R.sub.10 are independently hydrogen, alkyl or alkoxy, R.sub.17 or R.sub.19 is hydrogen or alkyl, and R.sub.18 is hydrogen, alkyl, aralkyl or aryl, are described for use as stabilizers for organic materials against thermal, oxidative or light-induced degradation.Type: GrantFiled: September 20, 1993Date of Patent: June 27, 1995Assignee: Ciba-Geigy CorporationInventor: Peter Nesvadba
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Patent number: 5412145Abstract: Compounds of general formula I: ##STR1## Wherein: R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are variables. These compounds have collagenase inhibition activity and are useful in the management of disease involving collagen degradation. Its uses include rheumatoide arthritis, corneal ulceration, osteoporosis, periodontitis, gingivitis and tumor invasion.Type: GrantFiled: December 23, 1993Date of Patent: May 2, 1995Assignee: British Bio-Technology LimitedInventors: M. J. Crimmin, A. H. Davidson, R. P. Beckett
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Patent number: 5401875Abstract: The invention concerns 2-aminocarboxylic acids and derivatives of formula ##STR1## processes for their preparation, as well as medicaments containing them for the inhibition of protein kinase C and thus for the prevention and/or treatment of heart and blood vessel diseases, such as thromboses, arterioscleroses, hypertension, of inflammatory processes, allergies, cancers, and certain degenerative damages of the central nervous system.Type: GrantFiled: April 22, 1991Date of Patent: March 28, 1995Assignee: Godecke AktiengesellschaftInventors: Uwe Trostmann, Johannes Hartenstein, Claus Rudolph, Christoph Schachtele, Hartmut Osswald, Gunter Weinheimer
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Patent number: 5395824Abstract: A prophylactic or therapeutic agent for malignant hypercalcemia, bone Paget's disease and osteoporosis is disclosed, which contains as an active ingredient a dipeptide derivative represented by formula:R.sup.1 NH--CH(R.sup.2)--CO--NH--CH(R.sup.3)--R.sup.4 (I)wherein R.sup.1 represents an aliphatic acyl group, a halogen-substituted aliphatic acyl group, or benzyloxycarbonyl group; R.sup.2 represents a lower alkyl group or an aralkyl group; R.sup.3 represents a lower alkyl group, an aralkyl group, or methylthioethyl group; R.sup.Type: GrantFiled: October 30, 1992Date of Patent: March 7, 1995Assignee: Suntory LimitedInventors: Naoki Higuchi, Masayuki Saitoh, Shinjiro Niwata, Yoshinobu Kiso, Yasuhiro Hayashi
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Patent number: 5387607Abstract: O-Benzyloxime ethers of the formula I ##STR1## where X is substituted or unsubstituted CH.sub.2, NOalkylY isO, S, NR.sup.5R.sup.1, R.sup.2, R.sup.5 are H, alkylZ.sup.1, Z.sup.2 are H, halogen, methyl, methoxy, cyanoR.sup.3, R.sup.4 are hydrogen, cyano, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl,N(R.sup.6).sub.2, where R.sup.6 is H, alkyl, substituted or unsubstituted phenyl,--CO--N(R.sup.7).sub.2, where R.sup.Type: GrantFiled: December 13, 1993Date of Patent: February 7, 1995Assignee: BASF AktiengesellschaftInventors: Siegbert Brand, Uwe Kardorff, Reinhard Kirstgen, Bernd Mueller, Klaus Oberdorf, Hubert Sauter, Gisela Lorenz, Eberhard Ammermann, Christoph Kuenast, Albrecht Harreus
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Patent number: 5374654Abstract: The invention relates to carbacyclin derivatives of Formula I ##STR1## wherein the various substituents are defined herein, including, inter alia,if R.sub.2 is a hydrogen atom, their salts with physiologically compatible bases, their cyclodextrin clathrates, and their use as medicinal agents.Type: GrantFiled: April 21, 1993Date of Patent: December 20, 1994Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Ulrich Klar, Bob Nieuweboer, Claus-Steffen Sturzebecher
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Patent number: 5364961Abstract: The invention includes selected novel optically active .alpha.-amino ketones which either are themselves useful or are intermediates for the preparation of known ketomethylene pseudopeptides useful as antibiotics, antibiotic enhancers, or enzyme inhibitors. Further, the present invention provides a method for dehydrogenation/asymmetrical hydrogenation to obtain essentially pure antipodes of ketomethylene pseudopeptides having two chiral centers.Type: GrantFiled: June 15, 1992Date of Patent: November 15, 1994Assignee: Monsanto CompanyInventor: John J. Talley
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Patent number: 5362902Abstract: Compounds of formula (I) are diuretic agents for treating various cardiovascular diseases including hypertension, heart failure and renal insufficiency.Type: GrantFiled: July 21, 1992Date of Patent: November 8, 1994Assignee: Pfizer Inc.Inventors: Ian T. Barnish, Keith James
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Patent number: 5359093Abstract: Immunoassay methods and reagents for the specific quantification of thyroxine in a test sample are disclosed employing antibodies prepared with thyroxine derivatives of the formula: ##STR1## wherein P is an immunogenic carrier material and X is a linking moiety. The present invention also describes the synthesis of unique labelled reagent of the formula: ##STR2## wherein Q is a detectable moiety and W is a linking moiety, preferably fluorescein or a fluorescein derivative.Type: GrantFiled: November 6, 1992Date of Patent: October 25, 1994Assignee: Abbott LaboratoriesInventors: Maciej Adamczyk, Donald D. Johnson, Phillip G. Mattingly, Diana E. Clarisse, Joan D. Tyner, Mary M. Perkowitz
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Patent number: 5354892Abstract: The invention relates to biaryl substituted 4-amino-butyric acid derivatives of formula I ##STR1## wherein COX and COX' independently represent carboxyl or carboxyl derivatized in form of a pharmaceutically acceptable ester or amide; R.sub.1 represents hydrogen, lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl-lower alkyl, aryl-lower alkyl, biaryl-lower alkyl, lower alkoxy, aryl-lower alkoxy, aryloxy, N-lower alkylamino, N,N-di-lower alkylamino, N-aryl-lower alkylamino, N,N-di-aryl-lower alkylamino, N-arylamino, N,N-diarylamino, lower alkanoylamino, aryl-lower alkanoylamino or aroylamino; R.sub.2 represents hydrogen, hydroxy, lower alkoxy, lower alkyl, aryl-lower alkyl, C.sub.3 -C.sub.Type: GrantFiled: January 25, 1993Date of Patent: October 11, 1994Assignee: Ciba-Geigy CorporationInventor: Gary Ksander
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Patent number: 5347036Abstract: Novel compounds which are 2,6-di-t-butylphenols substituted on the 4 position by an anilino group, which anilino group is substituted by a carboxyl substituent, a tetrazolyl substituent or an N-methyltetrazolyl substituent, are useful antiallergic agents. Pharmaceutical compositions containing and pharmacological methods of using such compounds are also disclosed, as are synthetic intermediates for preparing such compounds. Certain of the synthetic intermediates also exhibit useful antiallergic activity.Type: GrantFiled: May 26, 1993Date of Patent: September 13, 1994Assignee: Riker Laboratories, Inc.Inventor: Robert A. Scherrer