Nitrogen Attached Directly Or Indirectly To The Lactone Ring By Acyclic Nonionic Bonding Patents (Class 549/321)
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Patent number: 6333346Abstract: The present invention relates to ureido and thioureido derivatives of 4-amino-2(5H)-furanones and 4-amino-2(5H0-thiophenones for the treatment of tumors.Type: GrantFiled: June 2, 2000Date of Patent: December 25, 2001Assignee: Roche Diagnostics GmbHInventors: Ernesto Menta, Nicoletta Pescalli, Marco Conti, Gerd Zimmerman
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Patent number: 6331640Abstract: A compound of formula 1a which is useful for treating reperfusion injury, and salts, prodrugs, and related compounds.Type: GrantFiled: September 29, 1999Date of Patent: December 18, 2001Assignee: Hoffmann-La Roche Inc.Inventors: Nader Fotouhi, Paul Gillespie, Robert William Guthrie, Sherrie Lynn Pietranico-Cole, Weiya Yun
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Publication number: 20010041728Abstract: The present invention provides compounds of Formula 1 1Type: ApplicationFiled: March 30, 2001Publication date: November 15, 2001Inventors: Jackson B. Hester, Eldon George Nidy, Salvatore Charles Perricone, Toni-Jo Poel
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Patent number: 6297274Abstract: Novel nonpeptide endothelin I antagonists of Formula are described wherein R1 is unsubstituted or substituted cycloalkyl, phenyl, naphthyl or heteroaryl, R2 is unsubstituted or substituted alkyl, aryl or heteroaryl, R3 is unsubstituted or substituted alkyl, cycloalkyl, aryl or heteroayl, and R1 and/or R2 and/or R3 are independently substituted by a total of from 1 to 4 substituents which enhance aqueous solubility with the proviso that when R2 is alkyl and is substituted, the substituent is not oxygen at the &agr;-position of the furanone ring.Type: GrantFiled: August 4, 1998Date of Patent: October 2, 2001Assignee: Warner-Lambert CompanyInventors: Xue-Min Cheng, Annette Marian Doherty, William Chester Patt, Joseph Thomas Repine
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Patent number: 6294573Abstract: Compounds having the formula are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.Type: GrantFiled: January 27, 2000Date of Patent: September 25, 2001Assignee: Abbott LaboratoriesInventors: Michael L. Curtin, Yujia Dai, Steven K. Davidsen, Joseph F. Dellaria, Jr., Alan S. Florjancic, Jianchun Gong, Yan Guo, Howard R. Heyman, James H. Holms, Michael R. Michaelides, Jamie R. Stacey, Douglas H. Steinman, Carol K. Wada, Lianhong Xu
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Patent number: 6225288Abstract: Compounds represented by formula I: as well as pharmaceutically acceptable salts, esters and hydrates thereof are disclosed along with pharmaceutical compositions and methods of treatment. The compounds are useful as inhibitors of caspase-3, which is implicated in modulating apoptosis.Type: GrantFiled: March 16, 2000Date of Patent: May 1, 2001Assignee: Merk Frosst Canada & Co.Inventors: Yongxin Han, Andre Giroux, Erich Grimm, Renee Aspiotis, Sebastien Francoeur, Robert Zamboni, Petpiboon Prasit, Christopher Bayly, Dan McKay, Cameron Black
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Patent number: 6066667Abstract: The invention provides substituted furanone antiarthritic and analgesic pharmaceutical agents defined by Formula I, ##STR1## wherein: R.sup.1 is selected from the group consisting of(a) S(O).sub.2 CH.sub.3,(b) S(O).sub.2 NH.sub.2,(c) S(O).sub.2 NHC(O)CF.sub.3,(d) S(O)(NH)CH.sub.3,(e) S(O)(NH)NH.sub.2,(f) S(O)(NH)NHC(O)CF.sub.3,(g) P(O)(CH.sub.3)OH, and(h) P(O)(CH.sub.3)NH.sub.2 ;R.sup.2 and R.sup.3 independently are selected from(1) hydrogen,(2) halo,(3) C.sub.1 -C.sub.6 alkyl,(4) C.sub.1 -C.sub.6 alkoxy, and(5) C.sub.1 -C.sub.6 alkylthio;n is an integer from 1 to 3;m is an integor from 1 to 3;or a pharmaceutically acceptable salt thereof.Type: GrantFiled: August 17, 1999Date of Patent: May 23, 2000Inventor: Charles D. Ashbrook
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Patent number: 6037365Abstract: This invention provides a compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof. The invention also provides pharmaceutical compositions of such compounds and a method of treatment to inhibit aggregation of platelets.Type: GrantFiled: September 25, 1998Date of Patent: March 14, 2000Assignee: G.D. Searle & Co.Inventors: Philippe Roger Bovy, Joseph Gerace Rico, Thomas Edward Rogers
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Patent number: 5998468Abstract: Novel nonpeptide antagonists of endothelin (I) are described, as well as methods for the preparation and pharmaceutical compositions of the same, which are useful in treating elevated levels of endothelin, acute and chronic renal failure, hypertension, myocardial infarction, myocardial ischemia, cerebral vasospasm, cerebral ischemia, cerebral infarction, cirrhosis, septic shock, congestive heart failure, endotoxic shock, subarachnoid hemorrhage, arrhythmias, asthma, preeclampsia, atherosclerotic disorders including Raynaud's disease and restenosis, angina, cancer, pulmonary hypertension, ischemic disease, gastric mucosal damage, hemorrhagic shock, ischemic bowel disease, stroke, benign prostatic hyperplasia (BPH), and diabetes.Type: GrantFiled: December 15, 1997Date of Patent: December 7, 1999Assignee: Warner-Lambert CompanyInventors: Xue-Min Cheng, Annette Marian Doherty, William Chester Patt, Joseph Thomas Repine
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Patent number: 5990341Abstract: 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: December 24, 1996Date of Patent: November 23, 1999Assignee: Emory UniversityInventors: Dennis C. Liotta, Bharat Ramkrishna Lagu
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Patent number: 5969158Abstract: A compound having formula (1) for use as a medicament wherein n is 2 or 3; Y is O, S or NH; X is O, S or NH; and R is C.sub.1 -C.sub.18 alkyl or acyl which may be substituted.Type: GrantFiled: June 15, 1998Date of Patent: October 19, 1999Assignee: The University of NottinghamInventors: Barrie Walsham Bycroft, Herbert Fitzgerald Sewell, Gordon Sydney Anderson Birnie Stewart, Paul Williams
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Patent number: 5892061Abstract: A preparation process of isoimide comprising reacting a compound having one or more carboxyl group and one or more amide bond in the same molecule in the presence of a haloiminium salt and basic substance, and a preparation process of isoimide comprising reacting a compound having one or more carboxyl group with a compound having one or more amide bond in the presence of a haloiminium salt and basic substance are disclosed.Type: GrantFiled: November 21, 1997Date of Patent: April 6, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Kan Ikeda, Wataru Yamashita, Shoji Tamai
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Patent number: 5874464Abstract: Conformationally constrained diacylglycerol analogues, pharmaceutical compositions comprising such analogues, and methods of using such analogues as agonists and antagonists of protein kinase C.Type: GrantFiled: January 13, 1995Date of Patent: February 23, 1999Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Victor E. Marquez, Jeewoo Lee, Rajiv Sharma, Shaomeng Wang, George W. A. Milne, Marc C. Nicklaus, Peter M. Blumberg, Nancy E. Lewin
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Patent number: 5840918Abstract: Peptidomimetic compounds useful in the treatment of Ras-associated human cancers, and other conditions mediated by farnesylated or geranylgeranylated proteins; and synthetic intermediates thereof.Type: GrantFiled: March 19, 1997Date of Patent: November 24, 1998Assignee: Eisai Co., Ltd.Inventors: Michael D. Lewis, James J. Kowalczyk, Amy E. Christuk, Rulin Fan, Edmund M. Harrington, Xiaoning C. Sheng, Hu Yang, Ana Maria Garcia, Ieharu Hishinuma, Takeshi Nagasu, Kentaro Yoshimatsu
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Patent number: 5827879Abstract: This invention provides certain substituted 2,3-dihydrobenzofurylsulfonamide derivatives and methods for using them in the treatment of susceptible neoplasms in mammals. Also provided are certain novel pharmaceutical formulations employing these benzenesulfonamide derivatives in combination with a carrier.Type: GrantFiled: October 3, 1997Date of Patent: October 27, 1998Assignee: Eli Lilly and CompanyInventors: William J. Ehlhardt, James E. Ray, John E. Toth
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Patent number: 5776974Abstract: A compound having formula (1) for use as a medicament wherein n is 2 or 3; Y is O, S or NH; X is O, S or NH; and R is C.sub.1 -C.sub.18 alkyl or acyl which may be substituted.Type: GrantFiled: February 5, 1996Date of Patent: July 7, 1998Assignee: The University of NottinghamInventors: Barrie Walsham Bycroft, Herbert Fitzgerald Sewell, Gordon Sydney Anderson Birnie Stewart, Paul Williams
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Patent number: 5770731Abstract: A prodrug of the general formula FTLi-(PRT)m, where m is an integer from 1 to 5; FTLi is a ras inhibitor such as a farnesyltransferase inhibitor compound, such as Ia, Ib, Ic; and PRT represents m protecting groups or a precursor thereof, such as compound XVI, which are capable of being cleaved from the ras inhibitor by the action of a enzyme.Type: GrantFiled: April 19, 1996Date of Patent: June 23, 1998Assignee: Cancer Research Campaign Technology LimitedInventors: Caroline Joy Springer, Richard Marais
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Patent number: 5767147Abstract: This invention relates to novel haloenol lactone compounds. These compounds have the following general structure: ##STR1## in which Ar is an aryl group and Y is a haloenol lactone moiety. The compounds of the invention are useful for the specific measurement of particular isoenzymes of glutathione S-transferase. Measurement of glutathione S-transferase isoenzymes has importance in diagnostic medicine. The compounds of the invention are also useful for treatment of drug resistance in cancer and for preventing herbicide resistance in plants.Type: GrantFiled: April 21, 1995Date of Patent: June 16, 1998Assignee: The Regents of the University of CaliforniaInventors: A. Daniel Jones, Alyson E. Mitchell, Bruce D. Hammock, Jiang Zheng
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Patent number: 5731345Abstract: Seco-D steroid derivatives having the formula ##STR1## wherein R, R.sup.1, R.sup.2 and R.sup.3 have the meanings specified in the specification, useful as cardiovascular agents and pharmaceutical compositions containing same, are disclosed.Type: GrantFiled: April 15, 1996Date of Patent: March 24, 1998Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.AInventors: Mauro Gobbini, Patrizia Ferrari, Piero Melloni, Marco Torri
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Patent number: 5708169Abstract: The present invention provides for new 5-amidomethyl, .alpha.,.beta.-saturated and--unsaturated butyrolactone antibacterial agents of formula I ##STR1## characterized by 3-aryl substituents that include, for example, indolinyl and phenyl substituted with zero (0) to two(2) halogen atoms and substituted in the para position with, e.g., piperazinyl, thiomorpholinyl (and corresponding sulfoxide and sulfone), thiazolidinyl (and sulfoxide and sulfone), morpholinyl, azetidinyl, pyrrolidinyl, piperidinyl, pyrrolyl, azepinyl, troponyl, 3,7-diazabicyclo?3.3.0!octan-3-yl, bridged thiazinyl or bridged oxazinyl moieties. In those cases where a ring nitrogen is present, then this is substituted to form an amide, formamide, sulfonamide, urethane, or alkylated with a wide variety of moieties.Type: GrantFiled: September 5, 1996Date of Patent: January 13, 1998Assignee: Pharmacia & Upjohn CompanyInventors: Jackson B. Hester, Jr., Steven Joseph Brickner, Michael Robert Barbachyn, Douglas K. Hutchinson, Dana Scott Toops
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Patent number: 5705658Abstract: .delta.-Amino-.gamma.-hydroxy-.omega.-aryl-alkanoic acid amides of formula I ##STR1## and the salts thereof, have renin-inhibiting properties and can be used as antihypertensive medicinal active ingredients.Type: GrantFiled: February 14, 1997Date of Patent: January 6, 1998Assignee: Novartis CorporationInventors: Richard Goschke, Jurgen Klaus Maibaum, Walter Schilling, Stefan Stutz, Pascal Rigollier, Yasuchika Yamaguchi, Nissim Claude Cohen, Peter Herold
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Patent number: 5691373Abstract: Novel nonpeptide antagonists of endothelin I are described, as well as methods for the preparation and pharmaceutical compositions of the same, which are useful in treating elevated levels of endothelin, acute and chronic renal failure, hypertension, myocardial infarction, myocardial ischemia, cerebral vasospasm, cerebral ischemia, cerebral infarction, cirrhosis, septic shock, congestive heart failure, endotoxic shock, subarachnoid hemorrhage, arrhythmias, asthma, preeclampsia, atherosclerotic disorders including Raynaud's disease and restenosis, angina, cancer, pulmonary hypertension, ischemic disease, gastric mucosal damage, hemorrhagic shock, ischemic bowel disease, stroke, benign prosthatic hyperplasia (BPH), and diabetes.Type: GrantFiled: February 6, 1995Date of Patent: November 25, 1997Assignee: Warner-Lambert CompanyInventors: Kent Alan Berryman, Annette Marian Doherty, Jeremy John Edmunds, William Chester Patt, Mark Stephen Plummer, Joseph Thomas Repine
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Patent number: 5654445Abstract: .delta.-Amino-.gamma.-hydroxy-.omega.-aryl-alkanoic acid amides of formula I ##STR1## and the salts thereof, have renin-inhibiting properties and can be used as antihypertensive medicinal active ingredients.Type: GrantFiled: July 2, 1996Date of Patent: August 5, 1997Assignee: Ciba-Geigy CorporationInventors: Richard Goschke, Jurgen Klaus Maibaum, Walter Schilling, Stefan Stutz, Pascal Rigollier, Yasuchika Yamaguchi, Nissim Claude Cohen, Peter Herold
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Patent number: 5606078Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is free or esterified carboxy, hydroxymethyl or formyl,R.sub.2 and R.sub.4 are each independently of the other aliphatic, cycloaliphatic-aliphatic, araliphatic or heteroarylaliphatic radicals andR.sub.3 is azido, or amino that is aliphatically or araliphatically substituted and/or protected by an amino-protecting group,and the salts thereof, are valuable intermediates in the preparation of medicinal active ingredients, for example of compounds of formula II ##STR2## wherein R.sub.A is an aromatic or heteroaromatic radical,R.sub.2 and R.sub.4 are each independently of the other aliphatic, cycloaliphatic, cycloaliphaticaliphatic or araliphatic radicals,R.sub.3 is unsubstituted or N-mono- or N,N-di-lower alkylated or N-lower alkanoylated amino, andR.sub.B is an aliphatically, cycloaliphatically or heteroaromatically-aliphatically substituted amino group,and the salts thereof, which can be used, for example, as antihypertensives.Type: GrantFiled: April 4, 1995Date of Patent: February 25, 1997Assignee: Ciba-Geigy CorporationInventors: Richard G oschke, Peter Herold, Pascal Rigollier, J urgen K. Maibaum
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Patent number: 5593827Abstract: The compound N-(.beta.-ketocaproyl)L-homoserine lactone is shown to be an autoinducer that enhances gene expression in a wide variety of microorganisms. Use can be made of this property for diagnostic purposes, e.g., when gene expression causes bioluminescence or antibiotic production, or to promote bacterial growth. The invention claims use for these purposes of the compound and analogs of formula (I) where n is 2 or 3, each of X and Y is O, S or NH, and R is optionally-substituted C1-C12 alkyl or acyl. Some of these are also claimed as new compounds.Type: GrantFiled: October 18, 1993Date of Patent: January 14, 1997Assignee: The University of NottinghamInventors: Barrie W. Bycroft, Paul Williams, Gordon S. A. B. Stewart, Siri R. Chhabra, Paul Stead, Michael K. Winson, Philip J. Hill, Catherine E. D. Rees, Nigel J. Bainton
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Patent number: 5591872Abstract: Autoinducer molecules, e.g., N-(3-oxododecanoyl)homoserine lactone, for Pseudomonas aeruginosa are described. The molecules regulate gene expression in the bacterium. Therapeutic compositions and therapeutic methods involving analogs and/or inhibitors of the autoinducer molecules also are described. The molecules are useful for treating or preventing infection by Pseudomonas aeruginosa.Type: GrantFiled: August 9, 1993Date of Patent: January 7, 1997Assignee: The University of Iowa Research FoundationInventors: James P. Pearson, Kendall M. Gray, Luciano Passador, Kenneth D. Tucker, Anatol Eberhard, Barbara H. Iglewski, Everett P. Greenberg
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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: 5541321Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##Type: GrantFiled: March 30, 1995Date of Patent: July 30, 1996Assignee: Abbott LaboratoriesInventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
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Patent number: 5541320Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##Type: GrantFiled: March 30, 1995Date of Patent: July 30, 1996Assignee: Abbot LaboratoriesInventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
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Patent number: 5451686Abstract: Novel anti-inflammatory furanone compounds have the following formula: ##STR1## where R.sub.1 independently is H, or alkyl of 1 to 9 carbons and n is an integer having the values of 1 or 2, and where when n is 1 the R.sub.1 group is attached to the 5 position of the 2-furanone, when n is 2 then R.sub.1 is attached to both the 3 and 5 positions, with the proviso that when n is 1 then R.sub.1 is not H; Y.sub.1 is H, alkyl of 1 to 20 carbons, phenyl C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olefinic bonds, where R.sub.3 is H, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olefinic bonds, phenyl, halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, with the proviso that when Y.sub.1 is CO--OR.sub.3 or CONHR.sub.3 then R.sub.3 is not hydrogen; Y.sub.2 is H, an alkyl group of 1 to 25 carbons, or phenyl.Type: GrantFiled: April 15, 1994Date of Patent: September 19, 1995Assignee: Allergan, Inc.Inventor: Michael E. Garst
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Patent number: 5436339Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##Type: GrantFiled: July 14, 1992Date of Patent: July 25, 1995Assignee: Abbott LaboratoriesInventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
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Patent number: 5430056Abstract: Optically active or racemic compounds are provided having the formula ##STR1## where R.sub.1 is ##STR2## where Y is hydrogen, halogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.6 is C.sub.1 to C.sub.4 linear or branched alkyl; X is oxygen or sulfur; a is an integer from zero to 3; and n is an integer from 1 to 4. The compounds are capable of binding selectively to dopamine D.sub.2 receptors and are useful in treatment of disorders of the central nervous, cardiovascular and endocrine systems, such as intraocular pressure, schizophrenia and Parkinsonism, and for inducing anorexia and weight loss in humans and other mammals.Type: GrantFiled: February 23, 1994Date of Patent: July 4, 1995Assignee: Discovery Therapeutics, Inc.Inventors: James V. Peck, Gevork Minaskanian
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Patent number: 5430162Abstract: The invention provides compounds of formula ##STR1## wherein X, R and R.sup.1 are defined in the specification. These compounds are useful as antibiotic agents.Type: GrantFiled: March 21, 1994Date of Patent: July 4, 1995Assignee: American Cyanamid CompanyInventors: Phaik-Eng Sum, Ving J. Lee, Joseph J. Hlavka, Raymond T. Testa
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Patent number: 5326773Abstract: 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: July 5, 1994Assignee: Merck & Co., Inc.Inventors: S. Jane de Solms, Samuel L. Graham
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Patent number: 5312914Abstract: The invention relates to a novel process for the manufacture of 4-acetoxy-3-hydroxyethyl-azetidinone of the formula ##STR1## especially 4(R)-acetoxy-3(R)-(1'(R)-hydroxyethyl)-2-azetidinone, from enantiomerically pure compounds of the formula ##STR2## in which R.sup.1 represents lower alkyl and Z.sup.1 represents amino, arylmethylamino, acylamino or azido, by reduction of the C.dbd.C double bond and optionally of the arylmethylamino or azido group with hydrogen, epimerization, opening of the lactone ring, cyclisation to the .beta.-lactam, optionally after hydrolysis of the acylamino group, and oxidative decarboxylation of the original lactone carboxy group in the presence of an acetate-yielding agent. Compounds of the formula I can be used as starting materials for the manufacture of .beta.-lactam antibiotics. The invention also relates to novel intermediates and starting materials.Type: GrantFiled: August 27, 1992Date of Patent: May 17, 1994Assignee: Ciba-Geigy CorpInventors: Gottfried Sedelmeier, Jacques Bersier
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Patent number: 5294643Abstract: Novel cinnamamide derivatives and the salts thereof are provided. An antihyperlipidemic composition is also provided. The composition comprises an active ingredient which is at least one selected from the group consisting of the above-mentioned cinnamamide derivative and the pharmaceutically acceptable salt thereof.Type: GrantFiled: July 5, 1990Date of Patent: March 15, 1994Assignee: Kanegafuchi Kagaku Kogyo KabushikiInventors: Yoshihide Fuse, Kenji Fujii, Keiji Kameyama, Taizo Kawabe, Toshiaki Miwa, Ikuo Katsumi
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Patent number: 5274122Abstract: Homocysteine thiolactone derivatives in which the nitrogen is acylated with groups containing acidic functionalities have been synthesized. These include the succinyl, the carboxymethylglutaryl, the 3-phosphonopropionyl and the 3-sulfopropionyl derivatives. These thiolactones can be used to introduce a thiol functionality into proteins such as the outer membrane protein complex of Neisseria meninioitidis (OMPC) allowing conjugation with electrophilic ligands. This chemistry is similar to known N-acetyl-homocysteine thiolactone chemistry, but the pK.sub.a values are such that at pH 7, concomitant negative charge is introduced into the conjugate. Such negative charge neutralizes excess positive charge introduced when arginine- and lysine-rich peptides are bonded as ligands. In the case of OMPC, introduction of positive charge commonly effects irreversible precipitation of the conjugate. Conjugates prepared with the anionic thiolactones have improved solubility.Type: GrantFiled: October 15, 1992Date of Patent: December 28, 1993Assignee: Merck & Co., Inc.Inventors: Richard L. Tolman, Stephen Marburg, William J. Leanza
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Patent number: 5254697Abstract: The invention provides a novel process for the manufacture of enantiomerically-pure halolactones of the formula I which are useful for the production of certain 5-amino-4-hydroxyvaleric acid derivatives, themselves valuable intermediates in the production of compounds which are renin inhibitors. The process involves a diastereoselective alkylation of an oxazolidinone of the formula III, followed by a highly stereoselective and novel halolactonisation of an oxazolidinone of the formula II. Certain of the oxazolidinones of the formula II are novel and are provided as a further feature of the invention. The invention also provides a novel process for the production of the pharmaceutically-useful 5-amino-4-hydroxyvaleric acid derivatives of formula VI.Type: GrantFiled: June 4, 1990Date of Patent: October 19, 1993Assignee: Imperial Chemical Industries PLCInventor: David Waterson
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Patent number: 5239088Abstract: .alpha.-Amino-.gamma.-butyrolactones (homoserine lactones) are a central structural element in many biologically active compounds. The known syntheses for the preparation of optically active homoserine lactones from D- or L-methionine and D- or L-aspartic acid derivatives have disadvantages. Homoserine lactones I and their salts can be prepared enantioselectively according to the invention by catalytic hydrogenation of aldehydes II ##STR1## where R in the formulae is hydrogen, alkyl, alkenyl, alkynyl, it being possible for the aforementioned three radicals to have hetero atoms in the chain, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, benzyl, benzyloxycarbonyl, aryloxycarbonyl or arylsulfonyl, it being possible for the four last-mentioned radicals to be optionally substituted in the aryl moiety.Type: GrantFiled: February 6, 1992Date of Patent: August 24, 1993Assignee: Hoechst AktiengesellschaftInventors: Michael G. Hoffman, Hans-Joachim Zeiss
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Patent number: 5189035Abstract: The invention provides furanone derivatives of the general formula ##STR1## in which R.sup.1 represents a halogen atom or an optionally substituted alkyl or alkoxy group, R.sup.2 represents a halogen atom or an optionally substituted alkyl, aryl or heterocyclyl group, R.sup.7 represents a C.sub.1-4 alkyl group and Q represents an optionally substituted morpholino or amino group; processes for their preparation; compositions containing such compounds and their use as fungicides.Type: GrantFiled: April 2, 1992Date of Patent: February 23, 1993Assignee: Shell Research LimitedInventors: Jurgen Curtze, Guido Albert
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Patent number: 5185349Abstract: Novel lactone and lactam compounds which are useful to lower blood cholesterol levels in a patient, said compounds containing an arylcarboxamide or arylthiocarboxamide moiety.Type: GrantFiled: March 8, 1991Date of Patent: February 9, 1993Assignee: Warner-Lambert CompanyInventor: Corinne E. Augelli-Szafran
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Patent number: 5175313Abstract: The present invention provides a process for preparing dihydrofuranone derivative of the formula (I): ##STR1## wherein R.sup.1 and R.sup.3 are individually lower alkyl, and R.sup.2 is hydrogen or lower alkyl, by reacting a dihydrofuranone derivative of the formula(I): ##STR2## wherein R.sup.1 is as defined above, with a malonic acid derivative of the formula (II): ##STR3## wherein R.sup.2 and R.sup.3 are as defined above, in the presence of an alkalimetal alkoxide and/or an alkalimetal hydroxide.Type: GrantFiled: May 3, 1991Date of Patent: December 29, 1992Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Junichi Imuta, Aiichiro Ori, Noriaki Kihara
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Patent number: 5169976Abstract: Variously substituted 4-(biphen-2-ylmethylcarbamoyl)-3-hydroxybutyric acids and esters, also named as N-(biphen-2-yl)-3-hydroxyglutaramic acid derivatives, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.Type: GrantFiled: May 3, 1990Date of Patent: December 8, 1992Assignee: Pfizer Inc.Inventor: Peter A. McCarthy
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Patent number: 5155015Abstract: A silver halide photographic material contains in a hydrophilic colloid layer a 4-arylazooxazoline-5-one compound or/and a 2-arylazo-3-butene-4-olide compound in the form of a dispersion of fine solid particles or a composition with an oil or/and a polymer latex. The compounds not only can selectively color a particular layer alone but also can be speedily decolorized and/or eluted in the course of development processing. In addition, they have no undesirable effects on photographic characteristics.Type: GrantFiled: March 27, 1992Date of Patent: October 13, 1992Assignee: Fuji Photo Film Co., Ltd.Inventor: Yoshihiro Jimbo
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Patent number: 5140011Abstract: The compounds of the formula ##STR1## wherein A, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the significance given in claim 1, in the form of optically pure diastereomers, mixtures of diastereomers, diastereomeric racemates or mixtures of diastereomeric racemates as well as pharmaceutically usable salts thereof inhibit the activity of the natural enzyme renin and can accordingly be used in the form of pharmaceutical preparations in the control or prevention of high blood pressure and cardiac insufficiency.Type: GrantFiled: March 29, 1990Date of Patent: August 18, 1992Assignee: Hoffmann-La Roche, Inc.Inventors: Quirico Branca, Hans P. Marki, Werner Neidhart, Henri Ramuz, Wolfgang Wostl
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Patent number: 5099036Abstract: Disclosed are .alpha.-(.omega.-Cyanoalkanoyl)-.gamma.-butyrolactone represented by the formula: ##STR1## wherein n represents an integer of 7 to 11, and a method for producing the same, which comprises reacting .omega.-cyano fatty acid ester represented by the formula:NC--(CH.sub.2).sub.n --COOR (II)wherein R represents an alkyl group having 1 to 4 carbon atoms and n has the same meaning as in the above, with .gamma.-butyrolactone in the presence of alkali metal alcoholate represented by the formula:R'OM (III)wherein R' represents an alkyl group having 1 to 4 carbon atoms and M represents an alkali metal.Type: GrantFiled: March 11, 1991Date of Patent: March 24, 1992Assignees: Ube Industries, Ltd., Soda Aromaic Co., Ltd.Inventors: Hiroshi Yoshida, Noboru Kakeya, Masanori Kashiwagi
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Patent number: 5094681Abstract: Herbicidal 5H-furan-2-one derivatives of the formula ##STR1## in which X represents the radical OR.sup.1 or the radical ##STR2## q represents the number 0 or 1,R.sup.2 is optionally substituted aryl, andR.sup.3 and R.sup.6 are hydrogen or various organic radicals, with certain provisos and exceptions.Type: GrantFiled: August 30, 1990Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Gerd Kleefeld, Jurgen Bachmann, Peter Babczinski, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
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Patent number: 5091425Abstract: This invention concerns novel nitrogen derivatives of the formula I ##STR1## (and their pharmaceutically-acceptable salts), together with pharmaceutical compositions containing them. The nitrogen derivatives are inhibitors of the catalytic action of renin. The invention further concerns novel processes for the manufacture of said inhibitors.Type: GrantFiled: November 14, 1989Date of Patent: February 25, 1992Assignee: Imperial Chemical Industries plcInventors: Robert H. Bradbury, David Brown, David A. Roberts, David Waterson
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Patent number: 5059611Abstract: New 5-hydroxy-2-furanone compounds have anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.Type: GrantFiled: October 25, 1989Date of Patent: October 22, 1991Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 5045564Abstract: New 2-furanone compounds have calcium channel antagonist activity and are useful as anti-inflammatory agents and in treating psoriasis.Type: GrantFiled: October 25, 1989Date of Patent: September 3, 1991Assignee: Allergan, Inc.Inventor: Gary C. M. Lee