Nitrogen Or -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Hetero Ring Patents (Class 548/953)
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Patent number: 6313315Abstract: There is disclosed a method for producing an essentially enantiomerically pure N-protected-azetidine-2-carboxylic acid of formula (1): which method is characterized by: subjecting a crude enantiomerically excess N-protected-azetidine-2-carboxylic acid comprising said enantiomer represented by formula (1) in excess to the other enantiomer thereof to crystallization in an organic solvent selected from aromatic hydrocarbon, aliphatic ether, aliphatic alcohol, aliphatic ketone, aliphatic nitrile, aliphatic amide, aliphatic sulfoxide, aliphatic ester and a mixed solvent thereof, wherein R is: an optionally substituted alkyl, alicyclic or alicyclicalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, or a dialkylamino group, and absolute configuration of the asterisked asymmetric carbon atom is S or R.Type: GrantFiled: June 1, 2000Date of Patent: November 6, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuhiro Yamauchi, Hideki Ushio, Isao Kurimoto
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Patent number: 6303636Abstract: A compound of the formula wherein R1, R2 and Q are as defined above, useful in the treatment of a condition selected from the group consisting of arthritis, cancer, tissue ulceration, macular degeneration, restenosis, periodontal disease, epidermolysis bullosa, scleritis, and other diseases characterized by matrix metalloproteinase activity, AIDS, sepsis, septic shock and other diseases involving the production of TNF.Type: GrantFiled: July 22, 1999Date of Patent: October 16, 2001Assignee: Pfizer IncInventors: Ralph Pelton Robinson, Jr., Kim Francis McClure
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Publication number: 20010023244Abstract: There is provided EtO2C—CH2—(R)Cgl—Aze—Pab—OH, or a pharmaceutically-acceptable salt thereof, in a form which is substantially crystalline. It has been found that crystalline forms of EtO2C—CH2—(R)Cgl—Aze—Pab—OH have a high chemical and solid state stability when compared to amorphous forms of the compound.Type: ApplicationFiled: January 4, 2001Publication date: September 20, 2001Applicant: Astra AktiebolagInventors: Daniel Edvardsson, Lena Hedstrom, Anita Lundblad, Ursula Pettersson
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Publication number: 20010020006Abstract: The present invention relates to compounds of unstable inhibitors of dipeptidyl peptidase IV (DP IV), which compounds have the general formula A—B—C, whereinType: ApplicationFiled: December 21, 2000Publication date: September 6, 2001Inventors: Hans-Ulrich Demuth, J?ouml;rn Schimdt, Torsten Hoffmann, Konrad Glund
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Publication number: 20010020092Abstract: The present invention relates to a compound of the formula (I) 1Type: ApplicationFiled: December 7, 2000Publication date: September 6, 2001Inventors: Mark James Ford, Jan Vermehren
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Patent number: 6265397Abstract: There is provided compounds of formula I, wherein R1, Rx, Y, Ry, n and B have meanings given in the description which are useful as competitive inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required (e.g. thrombosis) or as anticoagulants.Type: GrantFiled: June 26, 1998Date of Patent: July 24, 2001Assignee: AstraZeneca ABInventors: Olle Karlsson, Marcel Linschoten, Jan-Erik Nyström
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Patent number: 6255301Abstract: There is provided compounds of formula I, wherein R1, R2, R3, Rx, Y, n and B have meanings given in the description which are useful as competitive inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required as in thrombosis or as anticoagulants.Type: GrantFiled: July 14, 1997Date of Patent: July 3, 2001Assignee: AstraZeneca ABInventors: David Gustafsson, Jan-Erik Nyström
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Patent number: 6225287Abstract: There is provided EtO2C—CH2—(R)Cgl—Aze—Pab—OH, or a pharmaceutically-acceptable salt thereof, in a form which is substantially crystalline. It has been found that crystalline forms of EtO2C—CH2—(R)Cgl—Aze—Pab—OH have a high chemical and solid state stability when compared to amorphous forms of the compound.Type: GrantFiled: November 30, 1999Date of Patent: May 1, 2001Assignee: Astra AktiebolagInventors: Daniel Edvardsson, Lena Hedström, Anita Lundblad, Ursula Pettersson
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Patent number: 6201126Abstract: Compounds of the formula (I) in which A represents N or a cyanomethylene radical, B represents S, O or NH and R1, R2, R3 and x have the meaning given in the description, are highly suitable for dyeing and printing high-molecular-weight materials, in particular automotive cover fabrics.Type: GrantFiled: June 2, 1997Date of Patent: March 13, 2001Assignee: Bayer AktiengesellschaftInventor: Manfred Lorenz
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Patent number: 6166224Abstract: A method for racemization of an optically active N-substituted azetidine-2-carboxylic acid ester of the formula (1): ##STR1## wherein * represents an asymmetric carbon atom, R.sup.1 represents an aryl,R.sup.2 represents a saturated hydrocarbon group which may be substituted,which is characterized byheating the ester at 100.degree. C. or higher, orsubjecting the ester to contact with a basic compound selected from an alkali metal hydride, an alkali metal alcoholate of tertiary alcohol and an organic amine.Type: GrantFiled: May 14, 1999Date of Patent: December 26, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Norihiko Hirata, Isao Kurimoto
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Patent number: 6153609Abstract: A compound of the formula ##STR1## wherein n, X, R.sup.3, R.sup.4 and Q are as defined above, useful in the treatment of a condition selected from the group consisting of arthritis, cancer, tissue ulceration, macular degeneration, restenosis, periodontal disease, epidermolysis bullosa, scleritis, and other diseases characterized by matrix metalloproteinase activity, AIDS, sepsis, septic shock and other diseases involving the production of TNF. In addition, the compounds of the present invention may be used in combination therapy with standard non-steroidal anti-inflammatory drugs (NSAID'S) and analgesics, and in combination with cytotoxic drugs such as adriamycin, daunomycin, cis-platinum, etoposide, taxol, taxotere and other alkaloids, such as vincristine, in the treatment of cancer.Type: GrantFiled: February 16, 1999Date of Patent: November 28, 2000Assignee: Pfizer IncInventors: Ralph P. Robinson, Todd A. Blumenkopf
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Patent number: 6150457Abstract: The present invention relates to compounds containing modified hydrazide groups and corresponding to formula I ##STR1## wherein R represents the residue obtained by removing the isocyanate groups from a monomeric polyisocyanate, a polyisocyanate adduct or an NCO prepolymer,X represents OR' or NHR' andR' represents a group which is inert to isocyanate groups under the conditions used to form the compound of formula I andn has a value of 2 to 6.The present invention also relates to one-component, thermoset coating compositions containing the compounds of formula I and a cross-linking component that is reactive with these compounds. Finally, the present invention relates coatings, sealants and adhesives prepared from these thermoset compositions.Type: GrantFiled: November 23, 1998Date of Patent: November 21, 2000Assignees: Bayer Corporation, Bayer AktiengesellscaftInventors: Sze-Ming Lee, Douglas A. Wicks, Eberhard Koenig, Carol L. Kinney, Karen M. Henderson
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Patent number: 6150535Abstract: The present invention has its object to provide a process for producing azetidine-2-carboxylic acid and an intermediate thereof, which is efficient and economical and suited for industrial practice.The present invention is related to a process for producing azetidine-2-carboxylic acid of the following formula (5), which comprises subjecting a 4-oxo-2-azetidinecarboxylic acid derivative represented by the general formula (1) to hydride reduction to give azetidine-2-methanol of the following formula (2), treating the same with an amino-protecting agent to give N-protected azetidine-2-methanol represented by the following general formula (3), treating this with an oxidizing agent to give N-protected azetidine-2-carboxylic acid represented by the following general formula (4) and, further, subjecting the amino-protecting group thereof to elimination.Type: GrantFiled: December 30, 1999Date of Patent: November 21, 2000Assignee: Kaneka CorporationInventors: Hiroshi Awaji, Shingo Matsumoto, Kenji Inoue, Kazuhiko Matsuo
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Patent number: 6143554Abstract: There is provided a process for producing an optically active N-substituted azetidine-2-carboxylic acid compound represented by the formula (2): ##STR1## by contacting a corresponding N-substituted azetidine-2-carboxylic acid ester of formula (2) with an enzyme derived from a microorganism selected from Arthrobacter SC-6-98-28 strain, Arthrobacter sp. ATCC21908 strain, Chromobacterium SC-YM-1 strain, and a mutant thereof. A process is also provided for preparing an optically active azetidine-2-carboxylic acid by eliminating the N-substituent of a N-substituted azetidine-2-carboxylic acid ester of formula (2).Type: GrantFiled: July 13, 1999Date of Patent: November 7, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiki Takashima, Junko Kudo, Ayumi Inoue, Motoo Hazama
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Patent number: 6143903Abstract: The invention relates to a process for the production of enantiomerically-pure AzeOH which comprises selective crystallisation of a diastereomerically-pure AzeOH-tartrate salt from a homogeneous solution of AzeOH, optically-active tartaric acid, an organic acid and an aldehyde, followed by liberation of the free amino acid.Type: GrantFiled: September 4, 1997Date of Patent: November 7, 2000Assignee: Astra AktiebolagInventors: Philipp Barth, Armin Pfenninger
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Patent number: 6124474Abstract: A process for preparing chiral isomers of N-protected 2-azetidinemethanol compounds, particularly N-(phenylmethyl)-2-azetidinemethanol and N-BOC-2-azetidinemethanol, and especially the (R)-isomers thereof, as well as O-substituted derivatives thereof.Type: GrantFiled: December 21, 1999Date of Patent: September 26, 2000Assignee: Abbott LaboratoriesInventors: Anthony R. Haight, John E. Lallaman, Gregory S. Wayne
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Patent number: 6121462Abstract: The invention is a process for the modification or substitution of aza suituted azetidines through acylative dealkylation.Type: GrantFiled: September 14, 1998Date of Patent: September 19, 2000Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Dave Paritosh
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Patent number: 6114543Abstract: The present invention provides a process for preparing optically active azetidine-2-carboxylic acids using readily available reagents of relatively low price in the industry. Thus, there is provided optically active azetidine-2-carboxylic acid, and a process for producing the same by subjecting optically active N-(alkylbenzyl)azetidine-2-carboxylic acid represented by the formula (1): ##STR1## to hydrogenolysis in the presence of a catalyst.Type: GrantFiled: August 4, 1998Date of Patent: September 5, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Hideki Ushio, Naoyuki Takano, Yukihiro Honda, Shinzo Seko, Motoo Hazama
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Patent number: 6066730Abstract: Disclosed herein is a method for reducing the rate of degradation of proteins in an animal comprising contacting cells of the animal with certain boronic ester and acid compounds. Also disclosed herein are novel boronic ester and acid compounds, their synthesis and uses.Type: GrantFiled: May 26, 1998Date of Patent: May 23, 2000Assignee: ProScript, Inc.Inventors: Julian Adams, Yu-Ting Ma, Ross Stein, Matthew Baevsky, Louis Grenier, Louis Plamondon
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Patent number: 6054594Abstract: Process for obtaining an enantiomerically enriched N-acylazetine-2-carboxylic acid by selectine crystallization of a diastereoisomeric salt formed by relcting an enantiomer of the N-acylazetidine-2-carboxylic acid and an enantiomer of 1-phenylethylamine.Type: GrantFiled: December 16, 1998Date of Patent: April 25, 2000Assignee: Astra ABInventors: Gerard Andrew Potter, Michael C. J. Harris
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Patent number: 6051568Abstract: There is provided amino acid derivative formula I, ##STR1## wherein p, q, R.sup.1, R.sup.2, R.sup.3, R.sup.4, Y, n and B have meanings given in the description which are useful as competitive inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required (e.g. thrombosis) or as anticoagulants.Type: GrantFiled: August 7, 1996Date of Patent: April 18, 2000Assignee: Astra AktiebolagInventors: David Gustafsson, Jan-Erik Nystrom
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Patent number: 5994351Abstract: A compound of the formula ##STR1## wherein n, X, R.sup.3, R.sup.4 and Ar are as defined above, useful in the treatment of a condition selected from the group consisting of arthritis, cancer, tissue ulceration, restenosis, periodontal disease, epidermolysis bullosa, scleritis and other diseases characterized by matrix metalloproteinase activity, AIDS, sepsis, septic shock and other diseases involving the production of TNF.Type: GrantFiled: July 27, 1998Date of Patent: November 30, 1999Assignee: Pfizer Inc.Inventors: Ralph P. Robinson, James P. Rizzi
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Patent number: 5986108Abstract: Disclosed herein are azetidin-2-one compounds which exhibit excellent cysteine proteinase inhibitory activity. The compounds are 4-substituted-3-{1 or 2 amino acid residue}-azetidin-2-ones of forumula I ##STR1## wherein AAR is a 1 or 2 acid residue, and R.sub.1 and R.sub.2 are as defined herein. The compounds can be used in the treatment of various diseases such as muscular dystrophy, bone resorption disorders, myocardial infarction and cancer metastasis.Type: GrantFiled: September 8, 1997Date of Patent: November 16, 1999Assignee: Synphar Laboratories, Inc.Inventors: Rajeshwar Singh, Nian En Zhou, Deqi Guo, Ronald G. Micetich
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Patent number: 5965565Abstract: The present invention is directed to certain piperidines, pyrrolidines, and hexahydro-1H-azepines of the general structural formula: ##STR1## wherein B is selected from: ##STR2## and R.sup.1, R.sup.1a, R.sup.2a, R.sup.3a, R.sup.3b, R.sup.4, R.sup.4a, R.sup.4b, R.sup.4c, R.sup.5, D, X, Y, n, x and y are as defined herein. These compounds promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such compounds as the active ingredient thereof are also disclosed.Type: GrantFiled: December 11, 1997Date of Patent: October 12, 1999Assignee: Merck & Co., Inc.Inventors: Meng H. Chen, Zhijian Lu, Ravi Nargund, Arthur A. Patchett, James R. Tata, Lihu Yang, Mu Tsu Wu
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Patent number: 5959123Abstract: The present invention is based on the discovery that certain 3,4-disubstituted-azetidin-2-one derivatives exhibit excellent cysteine proteinase inhibitory activity which can be used for treatment of different diseases such as muscular dystrophy, myocardial infarction, bone resorption, arthritis, cancer metastasis, pulmonary emphysema, septic shock, cerebral ischemia, memory function, Alzheimer and cataract, malaria, glomerular basement membrane degradation, bacterial infection, inflammatory diseases, parasitic infections, and viral infections. In accordance to the present invention, there is provided a 3,4-disubstituted-azetidin-2-one derivatives of formula I, wherein R.sub.1, R.sub.2 and R.sub.3 are as defined herein, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: September 22, 1997Date of Patent: September 28, 1999Assignee: Synphar Laboratories, Inc.Inventors: Rajeshwar Singh, Nian E. Zhou, Deqi Guo, Ronald G. Micetich
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Patent number: 5942630Abstract: The invention relates to a process for the production of enantiomerically-pure AzeOH which comprises selective crystallisation of a diastereomerically-pure tartrate salt thereof, followed by liberation of the free amino acid, as well as the compounds L-azetidine-2-carboxylic acid-D-tartrate and D-azetidine-2-carboxylic acid-L-tartrate.Type: GrantFiled: September 19, 1996Date of Patent: August 24, 1999Assignee: Astra ABInventors: Philipp Barth, Hugo Fritschi, Jan-Erik Nystrom, Armin Pfenninger
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Patent number: 5939561Abstract: The present invention relates to new process for the preparation of .beta.-phenylisoserine and its analogues of general formula: ##STR1## which are particularly useful for preparing taxane derivatives which have remarkable antitumour and antileukaemic activities.Type: GrantFiled: May 7, 1997Date of Patent: August 17, 1999Assignee: Rhone-Poulence Rorer S.A.Inventors: Jean-Dominique Bourzat, Alain Commercon
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Patent number: 5883093Abstract: The present invention relates to antimicrobial phenyloxazolidinone compounds having a pyrrolidinyl or azetidinyl moiety.Type: GrantFiled: April 23, 1997Date of Patent: March 16, 1999Assignee: Pharmacia & Upjohn CompanyInventors: Douglas K. Hutchinson, Steven J. Brickner, Michael R. Barbachyn, Mikio Taniguchi, Kiyotaka Munesada, Hiroyoshi Yamada
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Patent number: 5880291Abstract: The present invention provides a process for preparing optically active azetidine-2-carboxylic acids using readily available reagents of relatively low price in the industry. Thus, there is provided optically active azetidine-2-carboxylic acid, and a process for producing the same by subjecting optically active N-(alkylbenzyl)azetidine-2-carboxylic acid represented by the formula (1): ##STR1## to hydrogenolysis in the presence of a catalyst.Type: GrantFiled: September 5, 1997Date of Patent: March 9, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Hideki Ushio, Naoyuki Takano, Yukihiro Honda, Shinzo Seko, Motoo Hazama
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Patent number: 5856492Abstract: An efficient method for the quantitative preparation and isolation of a compound of formula I ##STR1## or its enantiomer, a chiral mediator used in enantioselective synthesis.Type: GrantFiled: January 5, 1998Date of Patent: January 5, 1999Assignee: Merck & Co., Inc.Inventors: Cheng Yi Chen, Feng Xu, Richard D. Tillyer, Dalian Zhao
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Patent number: 5824807Abstract: Azabicylobutane can be produced by reacting azetidines under aqueous conditions to eliminate aza and 3-position substituents to effect cyclization. New azetidinyl compounds are described which can be intermediates in the preparation of the azabicyclobutane.Type: GrantFiled: May 15, 1995Date of Patent: October 20, 1998Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Paritosh R. Dave, Thomas G. Archibald
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Patent number: 5824806Abstract: TNAZ can be prepared directly from N-tertiarybutyl-3,3-dinitroazetidine compounds. The compounds may be in the form of the tertiary amine or the quaternary amine. The reaction is in the presence of acetic anhydride and nitrate ions. It gives high yields and uses mild conditions.Type: GrantFiled: May 15, 1995Date of Patent: October 20, 1998Assignee: The United States of America as represented by the The Secretary of the ArmyInventors: Daniel Stec, III, Ralph L. Perez, Paritosh R. Dave, Thomas G. Archibald
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Patent number: 5808099Abstract: ADNAZ, N-acetyl, 3,3 dinitroazetidine, is a new compound and this invention provides the compound, its compositions, preparation and uses. As a compound, it forms a eutectic with TNAZ. It can be used to prepare other compounds. It can be readily nitrated to remove the acetyl group and form TNAZ.Type: GrantFiled: May 15, 1995Date of Patent: September 15, 1998Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Daniel Stec, III, Paritosh R. Dave
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Patent number: 5792787Abstract: Dithiocarboxylates, and in particular, dithiocarbamates, block the induced expression of the endothelial cell surface adhesion molecule VCAM-1, and are therefor useful in the treatment of cardiovascular disease, including atherosclerosis, post-angioplasty restenosis, coronary artery diseases, and angina, as well as noncardiovascular inflammatory diseases that are mediated by VCAM-1.Type: GrantFiled: June 7, 1995Date of Patent: August 11, 1998Assignee: Emory UniversityInventors: Russell M. Medford, R. Wayne Alexander, Margaret K. Offermann
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Patent number: 5780631Abstract: The invention concerns the compounds of the formulas: ##STR1## and protected forms and salts thereof which serve as starting materials in an improved method of synthesizing serine protease inhibitors. The invention further concerns an improved method for synthesizing serine protease inhibitors which utilizes the compounds.Type: GrantFiled: June 6, 1995Date of Patent: July 14, 1998Assignee: Astra AktiebolagInventors: Karl Thomas Antonsson, Ruth Elvy Bylund, Nils David Gustafsson, Nils Olov Ingemar Nilsson
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Patent number: 5776927Abstract: This invention relates to compounds which inhibit thrombin or factor Xa. The compounds contain an aldehyde functionality and a methionine sulfone or S-substituted cysteine sulfone residue. The compounds and their pharmaceutical compositions are useful for preventing thrombosis in mammals which are suspected of having a condition characterized by abnormal thrombosis.Type: GrantFiled: April 18, 1994Date of Patent: July 7, 1998Assignee: Corvas International, Inc.Inventors: Matthew M. Abelman, Robert J. Ardecky
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Patent number: 5777162Abstract: Described herein are compounds of Formula (XX) and Formula (XXIV), shown below, and processes of making same. ##STR1## wherein p is 0 ##STR2## wherein p is 1, and Y is chlorine or bromine.Type: GrantFiled: November 12, 1996Date of Patent: July 7, 1998Assignee: Zeneca LimitedInventors: Ian Richard Matthews, Christopher Richard Ayles Godfrey, John Martin Clough
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Patent number: 5773263Abstract: The antibiotic aflastatin A or its salt and its production by Streptomyces sp. MRI 142, FERM BP-5841 is presented. Aflastatin A is incorporated into a pharmaceutical composition and is employed as an aflatoxin contamination inhibitor, antimicrobial agent, antifungal agent and antitumor agent.Type: GrantFiled: March 3, 1997Date of Patent: June 30, 1998Assignee: Morinaga & Co., Ltd.Inventors: Makoto Ono, Akinori Suzuki, Akira Isogai, Shouhei Sakuda
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Patent number: 5763483Abstract: Novel carbocyclic compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and assay methods for detecting neuraminidase activity are also described.Type: GrantFiled: December 27, 1996Date of Patent: June 9, 1998Assignee: Gilead Sciences, Inc.Inventors: Norbert W. Bischofberger, Choung U. Kim, Willard Lew, Hongtao Liu, Matthew A. Williams
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Patent number: 5756426Abstract: Described herein are compounds of the formula I ##STR1## and the isomers thereof, in which either a) X is an N atom andY is OR.sub.11 or N(R.sub.12)R.sub.13, orb) X is CH andY is OR.sub.11,and in which furthermore:R.sub.11 is C.sub.1 -C.sub.4 alkyl;R.sub.12 and R.sub.13, independently, are hydrogen or C.sub.1 -C.sub.4 alkyl;A is an O atom or the group NR.sub.4 ; and whereinR.sub.1, R.sub.2 and R.sub.3 are as defined herein, are pesticidal active ingredients. They can be used for pest control, in particular as microbicides, insecticides and acaricides in agriculture, horticulture and in the hygiene sector.Type: GrantFiled: September 11, 1995Date of Patent: May 26, 1998Assignee: Novartis CorporationInventors: Hugo Ziegler, Stephan Trah, Saleem Farooq, Rene Zurfluh
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Patent number: 5747522Abstract: N-Acyl-.alpha.-aminocarboxylic acid derivatives of the formula ##STR1## wherein L, R' to R"' and Q have the significance given in the description, can be used for the treatment or prophylaxis of illnesses which are caused by the binding of adhesive proteins to blood platelets and by blood platelet aggregation and cell-cell adhesion. They are manufactured by cleaving off protecting groups in corresponding protected compounds or by converting the cyano group into the amidino group in corresponding nitriles.Type: GrantFiled: May 25, 1995Date of Patent: May 5, 1998Assignee: Hoffman-La Roche Inc.Inventors: Leo Alig, Paul Hadvary, Marianne Hurzeler, Marcel Muller, Beat Steiner, Thomas Weller
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Patent number: 5739131Abstract: A benzene derivative of the formula (I): ##STR1## wherein R.sup.1 is hydrogen, C.sub.1-6 -alkyl, C.sub.1-6 -haloalkyl, --NH.sub.2, --NHR.sup.21 ; R.sup.2 is hydroxyl, --OR.sup.22, three- to seven-membered saturated cycloaliphatic amino optionally interrupted by one or more nitrogen, oxygen or sulfur atoms, --NHR.sup.23, --N(R.sup.24).sub.2, --NH.sub.2 ; R.sup.4 is hydrogen, C.sub.1-6 -alkyl, or --C(.dbd.O)R.sup.25 ; R.sup.7 is --CO--, --SO.sub.2 --; R.sup.8 is --CO--, single bond; R.sup.12 is --R.sup.11 --R.sup.5 ; R.sup.11 is --N(R.sup.5)--, --NH--, --O--, --N(R.sup.26)--, --N(C(.dbd.O)R.sup.27)--, --N(C(.dbd.O)NH.sub.2)--, --N(C(.dbd.O)NHR.sup.28)--; R.sup.13 is hydrogen, C.sub.1-6 -alkyl, C.sub.1-6 -haloalkyl, --NHC(.dbd.O)(CH.sub.2).sub.m C.sub.6 H.sub.5, --NHC(.dbd.O)R.sup.29, --NHC(.dbd.O)CH(C.sub.6 H.sub.5).sub.2, --NH.sub.2, --NHR.sup.30, --(CH.sub.2).sub.n C.sub.6 H.sub.5 ; Z is C, CH, N; A is CH, N; R.sup.5 is hydrogen, --CH.sub.2 C.sub.6 H.sub.4 COOH, --CH.sub.2 C.sub.6 H.sub.4 COOR.sup.31, --CH.Type: GrantFiled: April 30, 1997Date of Patent: April 14, 1998Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Mikiro Yanaka, Fuyuhiko Nishijima, Hiroyuki Enari, Toshikazu Dewa, Toru Yamazaki, Michihito Ise
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Patent number: 5714485Abstract: Compounds of the invention have the following structure: ##STR1##Type: GrantFiled: January 16, 1997Date of Patent: February 3, 1998Assignee: Merck & Co., Inc.Inventors: William C. Lumma, Roger M. Freidinger, Stephen F. Brady, Philip E. Sanderson, Dong-Mei Feng, Terry A. Lyle, Kenneth J. Stauffer, Thomas J. Tucker, Joseph P. Vacca
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Patent number: 5696118Abstract: A benzene derivative of the formula (I): ##STR1## wherein R.sup.1 is hydrogen, C.sub.1-6 -alkyl, C.sub.1-6 -haloalkyl, --NH.sub.2, --NHR.sup.21 ; R.sup.2 is hydroxyl, --OR.sup.22, three- to seven-membered saturated cycloaliphatic amino optionally interrupted by one or more nitrogen, oxygen or sulfur atoms, --NHR.sup.23, --N(R.sup.24).sub.2, --NH.sub.2 ; R.sup.4 is hydrogen, C.sub.1-6 -alkyl, or --C(.dbd.O)R.sup.25 ; R.sup.7 is --CO--, --SO.sub.2 --; R.sup.8 is --CO--, single bond; R.sup.12 is --R.sup.11 --R.sup.5 ; R.sup.11 is --N(R.sup.5)--, --NH--, --O--, --N(R.sup.26)--, --N(C(.dbd.O)R.sup.27)--, --N(C(.dbd.O)NH.sub.2)--, --N(C(.dbd.O)NHR.sup.28)--; R.sup.13 is hydrogen, C.sub.1-6 -alkyl, C.sub.1-6 -haloalkyl, --NHC(.dbd.O)(CH.sub.2).sub.m C.sub.6 H.sub.5, --NHC(.dbd.O)R.sup.29, --NHC(.dbd.O)CH(C.sub.6 H.sub.5).sub.2, --NH.sub.2, --NHR.sup.30, --(CH.sub.2).sub.n C.sub.6 H.sub.5 ; Z is C, CH, N; A is CH, N; R.sup.5 is hydrogen, --CH.sub.2 C.sub.6 H.sub.4 COOH, --CH.sub.2 C.sub.6 H.sub.4 COOR.sup.31, --CH.Type: GrantFiled: June 1, 1995Date of Patent: December 9, 1997Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Mikiro Yanaka, Fuyuhiko Nishijima, Hiroyuki Enari, Toshikazu Dewa, Toru Yamazaki, Michihito Ise
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Patent number: 5693630Abstract: Compounds of the general formula ##STR1## or pharmaceutically acceptable salts thereof, wherein Z is a saturated or unsaturated 3 to 6 carbon chain,m is 2 or 3,R.sub.1 is a hydrogen atom, or a straight or branched C.sub.1-4 alkyl group,R.sub.2, R.sub.3 and R.sub.13 are situated in the ortho, meta, or para position of the phenyl ring and are the same or different and selected from the following groups: H, OH, OR.sub.14, halogen, CO.sub.2 R.sub.9, CN, CF.sub.3, NO.sub.2, NH.sub.2, COCH.sub.3,OSO.sub.2 CF.sub.3,OSO.sub.2 CH.sub.3,CONR.sub.10 R.sub.11, OCOR.sub.12, whereinR.sub.9, R.sub.12 and R.sub.14 is a straight or branched C.sub.1-4 alkyl group,R.sub.10 and R.sub.11 are the same or different and represents hydrogen or a straight or branched C.sub.1-6 alkyl group,R is 1) ##STR2## processes for their preparation, pharmaceutical preparations containing them and the use of the compounds in the treatment psychiatric disorders.Type: GrantFiled: October 26, 1994Date of Patent: December 2, 1997Assignee: Astra AktiebolagInventors: Stefan Bengtsson, Sven Hellberg, Nina Mohell, Lian Zhang, Gerd Hallnemo, David Jackson, Bengt Ulff
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Patent number: 5622984Abstract: Amidinophenol derivatives of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are (i) H, (ii) C1-4 alkoxy, (iv) C2-5 acyl, (v) halogen, (vi) NO.sub.2, (vii) benzoyl, (viii) COOR.sup.4 (in which R.sup.4 is C1-3 alkyl); A is bond, C1-4 alkylene, --C(R.sup.5).dbd.C(R.sup.6)--(in which R.sup.5 and R.sup.6 are H or C1-4 alkyl; R.sup.3 is (i) CON(R.sup.7)(R.sup.8), (ii) CON(R.sup.9)--CH(R.sup.7)(R.sup.8) or (iii) ##STR2## in which R.sup.7 and R.sup.8 are (1) H,(2) phenyl, (3) C7-10 phenylalkyl, (4) phenyl or C7-10 phenylalkyl substituted by 1 or 2 C1-4 alkyl, halogen or R.sup.11 --COOR.sup.12 (in which R.sup.11 is bond, C1-8 alkylene, C2-8 alkenylene, C2-8 alkynylene; R.sup.12 is H, C1-4 alkyl, C7-10 phenylalkyl, phenyl, allyl, propargyl), (5) C1-10 alkyl, (6) C2-10 alkenyl having 1 to 3 double bonds, (7) C2-10 alkynyl having 1 or 2 triple bonds, (8) R.sup.11a --COXR.sup.12 (in which R.sup.Type: GrantFiled: March 1, 1995Date of Patent: April 22, 1997Assignee: Ono Pharmaceutical Company, LimitedInventors: Hisao Nakai, Masanori Kawamura, Tsumoru Miyamoto
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Patent number: 5610297Abstract: A novel class of peptide .alpha.-ketoamides useful for selectively inhibiting serine proteases, selectively inhibiting cysteine proteases, generally inhibiting all serine proteases, and generally inhibiting all cysteine proteases, having the formula M.sub.1 -AA-NH--CHR.sub.2 --CO--CO--NR.sub.3 R.sub.4, M.sub.1 -AA.sub.2 -AA.sub.1 -CO--NR.sub.3 R.sub.4, M.sub.1 -AA-AA-AA-CO--NR.sub.3 R.sub.4, M.sub.1 -AA-AA-AA-AA-CO--NR.sub.3 R.sub.4, or M.sub.1 -AA-CO--NR.sub.3 R.sub.4.Type: GrantFiled: October 6, 1995Date of Patent: March 11, 1997Assignee: Georgia Tech Research Corp.Inventor: James C. Powers
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Patent number: 5602101Abstract: This invention relates to L-Arginine aldehyde derivatives, pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors and thromboembolic disorder agents.Type: GrantFiled: October 5, 1994Date of Patent: February 11, 1997Assignee: Eli Lilly and CompanyInventors: Aaron L. Schacht, Robert T. Shuman, Gerald F. Smith, James H. Wikel, Michael R. Wiley
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Patent number: 5580988Abstract: New N-nitro, 3 substituted azetidine compounds are disclosed and these are sed in processes to prepare TNAZ.Type: GrantFiled: May 15, 1995Date of Patent: December 3, 1996Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Paritosh R. Dave
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Patent number: 5536723Abstract: The invention relates to novel S-nitroso derivatives of ACE inhibitors and to pharmaceutical compositions comprising the S-nitrosothiol derivatives of the invention together with a pharmaceutically acceptable carrier.The invention also relates to methods for treating various pathophysiological conditions including acute myocardial infarction, left ventricular dysfunction without overt heart failure, hypertension, pulmonary hypertension, congestive heart failure, angina pectoris, vascular thrombosis, Raynauds syndrome, scleroderma, toxemia of pregnancy, acute renal failure, diabetic nephropathy, and renal artery stenosis, and to methods of inhibiting ACE and effecting vasodilation comprising administering the S-nitrosothiol derivatives of the ACE inhibitors of the invention to an animal.Type: GrantFiled: October 6, 1994Date of Patent: July 16, 1996Assignee: Brigham & Women's HospitalInventors: Joseph Loscalzo, John Cooke