Oxy In Acid Moiety Patents (Class 560/42)
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Preparation of a mannich base intermediate for 2-[(4-heterocyclic-phenoxymethyl)-phenoxy]-alkanoates
Patent number: 6136972Abstract: A Mannich base intermediate for 2-[(4-heterocyclic-phenoxymethyl)-phenoxyl]-alkanoates and methods for its preparation are provided. A method for preparation of an alkyl 2-[2-(secondary amino methyl)-5-alkylphenoxy]-alkanoate comprises the steps of: reacting a mixture of m-alkyl phenol, a secondary amine, and an aldehyde, with or without a catalyst, in a first solvent at reflux temperatures to form a 2-[(secondary amino)methyl]-5-alkylphenol. That product is then reacted with an alkyl 2-haloalkanoate, and an alkali metal carbonate, with or without a second catalyst in a second solvent at reflux temperatures to form the 2-[2-(secondary amino methyl)-5-alkylphenoxy]-alkanoate. The aldehyde may be paraformaldehyde, aqueous formaldehyde, formaldehyde, or polymerized acetal derivatives thereof. The first solvent may be acetonitrile or toluene. The catalyst may be an acid catalyst or a base catalyst.Type: GrantFiled: February 22, 2000Date of Patent: October 24, 2000Assignee: FMC CorporationInventors: Gerard A. Crispino, Mark R. Diener -
Patent number: 6136999Abstract: A chemical compound having the formula: ##STR1## wherein P.sub.1 is a hydroxyl protecting group, R.sub.1 may be H or electron withdrawing group, R.sub.2 may be H or electron withdrawing group, R.sub.3 may be H or electron withdrawing group, R.sub.4 may be H or electron withdrawing group, R.sub.5 may be H or electron withdrawing group, R.sub.6 may be an alkyl group, an olefinic group, an aromatic group, Ph, PhCH.sub.2, an O-alkyl group, an O-olefinic group, an O-aromatic group, O--Ph, or O--CH.sub.2 Ph.Type: GrantFiled: June 21, 1999Date of Patent: October 24, 2000Assignee: NaPro BioTherapeutics, Inc.Inventors: Madhavi C. Chander, James D. McChesney, Jan Zygmunt
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Patent number: 6100423Abstract: The present invention is directed to compounds of the formula ##STR1## where R.sup.1 is BOC or H, R is H or lower alkyl; X and Y are the same or different halo atoms selected from the group consisting of Cl, Br or I and pharmaceutically acceptable salts and isomers thereof.Type: GrantFiled: March 3, 1999Date of Patent: August 8, 2000Assignee: G. D. Searle & Co.Inventors: Joe T. Collins, Balekudru Devadas, Hwang-fun Lu, James W. Malecha, Julie Marion Miyashiro, Srinivasan Nagarajan, Joseph Gerace Rico, Thomas E. Rogers
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Patent number: 6075051Abstract: A method for protecting a crop against fungal diseases by inducing local and systemic resistance of the crop comprising applying to the crop or its locus a composition containing an effective amount of at least one .beta.-aminobutyric acid or .beta.-amino valeric acid and salts and derivatives thereof.Type: GrantFiled: October 29, 1998Date of Patent: June 13, 2000Assignee: Agrogene Ltd.Inventor: Yigal Cohen
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Patent number: 6054457Abstract: This invention relates to new benzamide derivatives having a vasopressin antagonistic activity, etc, and represented by general formula (I): ##STR1## wherein R.sup.1 is aryl optionally substituted with lower alkoxy, etc., R.sup.2 is lower alkyl, etc.,R.sup.3 is hydrogen, etc.,R.sup.4 is lower alkoxy, etc.,R.sup.5 is hydrogen, etc.,A is NH, etc.,E is ##STR2## etc., X is --CH.dbd.CH--, --CH.dbd.N--, or S, andY is CH or N,and pharmaceutically acceptable salts thereof, to processes for preparation thereof and to a pharmaceutical composition comprising the same.Type: GrantFiled: December 9, 1997Date of Patent: April 25, 2000Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Hiroyuki Setoi, Takehiko Ohkawa, Tatsuya Zenkoh, Hitoshi Sawada, Kentaro Sato, Hirokazu Tanaka
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Patent number: 6037472Abstract: Compounds of formula (I) ##STR1## and their pharmaceutically acceptable salts inhibit matrix metalloproteases, such as stromelysin, gelatinase, matrilysin and collagenase, and are useful in the treatment of mammals having disease-states alleviated by the inhibition of such matrix metalloproteases.Type: GrantFiled: November 22, 1994Date of Patent: March 14, 2000Assignee: Syntex (U.S.A.) Inc.Inventors: Arlindo Lucas Castelhano, Steven Lee Bender, Judith Gail Deal, Stephen Horne, Teng J. Liak, Zhengyu Yuan
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Patent number: 6028205Abstract: Taxane derivatives having alternative C2 substituents.Type: GrantFiled: December 8, 1997Date of Patent: February 22, 2000Assignee: Florida State UniversityInventors: Robert A. Holton, Chunlin Tao
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Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its conversion to C-13 sidechain of taxanes
Patent number: 6025516Abstract: The present invention provides an efficient route to the C-13 side chain of the anti-cancer drug paclitaxel (TAXOL) and its analogs. The process includes the resolution of racemic erythro 2-hydroxy-3-amino-3-phenylpropionamide by diastereomeric crystallization and its conversion via various intermediates to the threo-ethylester and threo-methylester isomers.Type: GrantFiled: October 14, 1998Date of Patent: February 15, 2000Assignee: Chiragene, Inc.Inventors: Sowmianarayanan Ramaswamy, Venkat G. Reddy, Yalin Luo -
Patent number: 6017956Abstract: The present invention relates to a compound of the formula (I): ##STR1## wherein Ar.sup.1, Ar.sup.2, Ar.sup.3 and Ar.sup.4 represent an aryl group or a heteroaromatic ring group; A represents a hydrocarbon group which may be substituted; X and Y represent an oxygen atom, a sulfur atom, a carbonyl group or a group of the formula --CHR.sup.a -- (wherein R.sup.a is a hydrogen atom or a lower alkyl group) or --NR.sup.b -- (wherein R.sup.b is a hydrogen atom or a lower alkyl group), or X and Y together represent a vinylene group or an ethynylene group; R.sup.1, R.sup.2, R.sup.3, R.sup.8 and R.sup.9 represent a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group or a lower alkoxy group; R.sup.4 and R.sup.Type: GrantFiled: March 25, 1998Date of Patent: January 25, 2000Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Yoshikazu Iwasawa, Tetsuya Aoyama, Kumiko Kawakami, Sachie Arai, Toshihiko Satoh, Yoshiaki Monden
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Patent number: 5998401Abstract: A class of substituted phenoxy naphthalene compounds of the structure: ##STR1## where n is 2 or 3; R.sup.1 is hydrogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, phenoxycarbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl, or C.sub.2 -C.sub.6 alkoxy-sulfonyl; R.sup.2 is is hydrogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, phenoxycarbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl, or C.sub.2 -C.sub.6 alkoxy-sulfonyl, or halo; and R.sup.3 is 1-piperidinyl, 1-pyrollidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino; are useful in the treatment of pathological conditions associated with post-menopause including osteoporosis, endometriosis, uterine fibroid disease, cardiovascular disease (particularly hyperlipidemia), and hormonally-dependent cancers (particularly breast and uterine cancer).Type: GrantFiled: February 28, 1995Date of Patent: December 7, 1999Assignee: Eli Lilly and CompanyInventor: Alan D. Palkowitz
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Patent number: 5981585Abstract: Compounds of the formula I ##STR1## and the isomers thereof, in which either a) X is an N atom and Y is OR.sub.11 or N(R.sub.12)R.sub.13, orb) X is CH and Y 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: November 12, 1997Date of Patent: November 9, 1999Assignee: Novartis Finance CorporationInventors: Hugo Ziegler, Stephan Trah, Saleem Farooq, Rene Zurfluh
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Patent number: 5965558Abstract: Y--X--C(R').dbd.C(R")COOR"'(A1)The present invention relates to novel protein tyrosine phosphatase modulating compounds having the general structure shown in Formula (A1), to methods for their preparation, to compositions comprising the compounds, to their use for treatment of human and animal disorders, to their use for purification of proteins or glycoproteins, and to their use in diagnosis. The invention relates to modulation of the activity of molecules with phosphotyrosine recognition units, including protein tyrosine phosphatases (PTPases) and proteins with Src-homology-2 domains, in in vitro systems, microorganisms, eukaryoic cells, whole animals and human beings. R' and R" are independently selected from the group consisting of hydrogen, halo, cyano, nitro, trihalomethyl, alkyl, arylalkyl. R"' is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, arylalkyl. X is aryl. Y is selected from hydrogen or ##STR1## wherein (*) indicates a potential point of attachment to X.Type: GrantFiled: October 29, 1997Date of Patent: October 12, 1999Assignee: Ontogen CorporationInventors: Adnan Mjalli, Sepehr Sarshar, Xiaodong Cao, Farid Bakir
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Patent number: 5965592Abstract: Compounds of the formula ##STR1## and their salts, in which R.sub.1, is a C.sub.1 -C.sub.7 aliphatic hydrocarbon radical; X.sub.1 is --CO; X.sub.2 is a divalent aliphatic hydrocarbon radical which comprises an ethyl group and an alkylene of 2 to 6 carbon atoms; R.sub.2 is hydroxy, carboxy or alkoxycarbonyl in which alkoxy is from 1 to 7 carbon atoms; X.sub.3 is a divalent aliphatic hydrocarbon; R.sub.3 is carboxyl or 5-tetrazolyl; and the rings A and B independently of one another are otherwise unsubstituted; can be prepared in a known manner and may be used as active ingredients for medicaments.Type: GrantFiled: July 29, 1998Date of Patent: October 12, 1999Assignee: Novartis CorporationInventors: Peter Buhlmayer, Franz Ostermayer, Tibur Schmidlin
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Patent number: 5958981Abstract: A .gamma.-diketone compound represented by the following formula (I) and a pharmaceutically acceptable salt and solvate thereof having platelet aggregation inhibitory activity is disclosed: ##STR1## wherein B is --Z--(CH.sub.2).sub.q COOR.sup.Type: GrantFiled: March 27, 1998Date of Patent: September 28, 1999Assignee: Meiji Seika Kabushiki KaishaInventors: Tomoaki Miura, Eiki Shitara, Shokichi Ohuchi, Kiyoaki Katano
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Patent number: 5952386Abstract: The present invention provides dihalopropene compounds of the general formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl or the like; L is C(.dbd.O)NH or the like; R.sub.2, R.sub.3 and R.sub.4 are independently halogen or the like; R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen or the like; m is an integer of 0 to 4; n is an integer of 0 to 2; X is chlorine or the like; Y is oxygen or the like; and Z is oxygen or the like, which have excellent insecticidal activity so that they are satisfactorily effective for the control of noxious insects.Type: GrantFiled: September 24, 1997Date of Patent: September 14, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Sanshiro Matsuo, Taro Hirose, Keiichi Izumi, Masaya Suzuki, Noriyasu Sakamoto, Kazunori Tsushima, Shigeru Saito, Hirotaka Takano
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Patent number: 5939578Abstract: This invention is related to novel vasomolol, compounds of this invention have the following formula wherein R.sub.1 represents C.sub.1-4 alkyl group. ##STR1## vasomolol is an ultra short-acting and vasodilatory selective .beta..sub.1 -adrenoceptor antagonist, and is devoid of ISA.Vasomolol is an utra short acting and vasodilatory selective .beta..sub.1 -adrenoceptor antagonist, and is devoid of IA. The ultra short-acting and vsodilatory .beta..sub.1 -adrenoceptor blocking activities of vasomolol-a guaiacoxypropanolamine derivative of vanillic acid ethyl ester--were studied. Vasomolol (0.5, 1.0, 3.0 mg/kg, I.v.) produced a dose-dependent bradycardia rsponse, and particularly a hypotensive action with an ultra short-acting property in pentobarbital-anesthetized normotensive rats. Vasomolol's steady-state of .beta.-blockade was attained within 10 min after initiation of an infuson and a rapid recovery from blockade took place after termination of the infusion. In isolated rat aorta, vasomolol (10.sup.-6 M-10.Type: GrantFiled: June 21, 1996Date of Patent: August 17, 1999Assignee: Tong-Ho LinInventor: Ing-Jun Chen
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Patent number: 5916922Abstract: A class of novel phenyl glyoxamides is disclosed together with the use of such compounds for inhibiting sPLA.sub.2 mediated release of fatty acids for treatment of conditions such as septic shock.Type: GrantFiled: November 24, 1997Date of Patent: June 29, 1999Assignee: Eli Lilly and CompanyInventors: Theodore Goodson, Jr., Richard Waltz Harper, David Kent Herron
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Patent number: 5902887Abstract: Compounds formed by reacting a protected amino acid with an alkali metal enolate of an alkyl acetate are reacted with a halogenating agent for halogenation of the 2-position, or a protected amino acid is reacted with an alkali metal enolate of an alkyl halogenoacetate, to form a 4-amino-3-oxo-2-halogenobutanoic acid ester derivative, and hydrolysis and decarboxylation are conducted to produce a 3-amino-2-oxo-1-halogenopropane derivative or its salt. The present method is a useful process for producing a 3-amino-2-oxo-1-halogenopropane derivatives which can easily be converted to a 3-amino-1,2-epoxypropane.Type: GrantFiled: April 14, 1998Date of Patent: May 11, 1999Assignee: Ajinomoto Co., Inc.Inventors: Yutaka Honda, Satoshi Katayama, Kunisuke Izawa, Masakazu Nakazawa, Takayuki Suzuki, Naoko Kanno
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Patent number: 5888721Abstract: The invention features two novel antibiotics, termed 15352A and 15352B, having the structures shown in the figures.Type: GrantFiled: July 3, 1996Date of Patent: March 30, 1999Assignee: Millennium Pharmaceuticals, Inc.Inventors: David Rothstein, Nagraj Mani, Zhi-Dong Jiang
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Patent number: 5886022Abstract: Inhibitors for matrix metalloproteases, pharmaceutical compositions containing them, and a process for using them to treat a variety of physiological conditions. The compounds of the invention have the generalized formula ##STR1## wherein each T is a substituent g roup; x is 0, 1, or 2; the group D represents ##STR2## the subscript "e" is 2 or 3; the group R.sup.14 represents a variety of possible substituent groups of the cycloalkyl ring between D and G; the subscript "k" is 0-2; and the group G represents M, ##STR3## in which M represents --CO.sub.2 H, --CON(R.sup.11).sub.2, or --CO.sub.2 R.sup.12 ; and R.sup.13 represents any of the side chains of the 19 noncyclic occurring amino acids.Type: GrantFiled: May 30, 1997Date of Patent: March 23, 1999Assignee: Bayer CorporationInventors: Harold Clinton Eugene Kluender, William Harrison Bullock, Brian Richard Dixon, Stephan Schneider, Michael Christopher VanZandt, Scott McClelland Wilhelm, Donald John Wolanin
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Patent number: 5877297Abstract: Boron compound completing reagents, intermediate reagents of those reagents and methods of synthesizing these reagents. These reagents, including those shown as General Formula CII may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain up to about 0 to 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one of intermediate amide and disulfide moieties, and a polyethylene glycol chain of from 3 to 12 carbon equivalents in length; group R.sub.2 is one of an alkyl and a methylene with an electronegative moiety; and BAS is a biologically active species.Type: GrantFiled: October 22, 1997Date of Patent: March 2, 1999Assignee: Prolinx, Inc.Inventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund
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Patent number: 5872224Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIV, and General Formula CVI. In one embodiment, the reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain of up to about 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one of intermediate amide and disulfide moieties, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; group R.sub.3 is selected from one of an H, an alkyl, and a methylene or ethylene moiety with an electronegative substituent; and BAS and BAS* are biologically active species.Type: GrantFiled: October 22, 1997Date of Patent: February 16, 1999Assignee: Prolinx, Inc.Inventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund
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Patent number: 5869623Abstract: Boron compound complexing reagents, intermediate reagents of those reagents, and methods of synthesizing these reagents are disclosed. These reagents, including those shown as General Formula II may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain of up to about 6 carbon equivalents in length, an unbranched saturated or unsaturated chain from about 6 to 18 carbon equivalents in length with at least one intermediate amide or disulfide moieties, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; group R.sub.2 is one of an alkyl and a methylene group with an electronegative moiety; and BAS is a biologically active species.Type: GrantFiled: October 22, 1997Date of Patent: February 9, 1999Assignees: Systemix, Prolinx, Inc.Inventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
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Patent number: 5859295Abstract: This invention relates to canvanine analogs, their pharmaceutical compositions, and a method for treatment of cancer, particularly pancreatic cancer.Type: GrantFiled: June 18, 1996Date of Patent: January 12, 1999Assignee: University of Kentucky Research FoundationInventors: Peter A. Crooks, Gerald A. Rosenthal
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Patent number: 5859210Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula IV and General Formula VI. In one embodiment, the reagent of General Formula IV may be used to form a complex with a boron compound, such as a complex shown in General Formula VI. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain of up to about 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one of intermediate amide or disulfide moieties, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; group R.sub.3 is selected from one of an H, an alkyl, and a methylene or ethylene moiety with an electronegative substituent; and BAS and BAS* are biologically active species.Type: GrantFiled: October 22, 1997Date of Patent: January 12, 1999Assignees: Prolinx, Inc., SystemixInventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
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Patent number: 5847192Abstract: Boron compound complexing reagents and methods of synthesizing these reagents are disclosed. These reagents, including those shown as General Formula I and General Formula II may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof.Type: GrantFiled: August 5, 1996Date of Patent: December 8, 1998Assignees: Prolinx, Inc., SystemixInventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
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Patent number: 5837878Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIII, General Formula CIV, and General Formula CVI. In one embodiment, the reagents of General Formula CIII may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula CIV. The reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI.Type: GrantFiled: August 5, 1996Date of Patent: November 17, 1998Assignee: Prolinx, Inc.Inventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund
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Patent number: 5801195Abstract: Novel aryl amides are inhibitors of tumor necrosis factor .alpha. and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is N-benzoyl-3-amino-3-(3',4'-dimethoxyphenyl)propanamide.Type: GrantFiled: December 30, 1994Date of Patent: September 1, 1998Assignee: Celgene CorporationInventors: George W. Muller, Mary Shire, David I. Stirling
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Patent number: 5776977Abstract: Compounds of formula I, ##STR1## wherein the substituents R.sub.1 -R.sub.4 and a have the given meanings and show an activity against inflammatory conditions.Type: GrantFiled: August 5, 1996Date of Patent: July 7, 1998Assignee: Hoechst AktiengesellschaftInventors: Ramachandra Ganapati Naik, Vilas Narayan Mumbaikar, Rangarajan Vasumathy, Aftab Dawoodbhai Lakdawala, Mandakini Vithalrao Shirole, Bansi Lal, Jurgen Blumbach, Klaus Ulrich Weithmann, Robert Ryder Bartlett
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Patent number: 5777148Abstract: Boron compound complexing reagents, intermediate reagents of those reagents and methods of synthesizing these reagents are disclosed. These reagents, including those shown as General Formula I and General Formula II may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof.Type: GrantFiled: August 5, 1996Date of Patent: July 7, 1998Assignee: Prolinx, Inc.Inventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund
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Patent number: 5770620Abstract: The present invention provides novel protein tyrosine phosphatase modulating compounds having an aryl acrylic acid structure, compositions comprising the compounds, and methods of making and using the same.Type: GrantFiled: October 16, 1995Date of Patent: June 23, 1998Assignee: Ontogen CorporationInventors: Adnan M. M. Mjalli, Xiaodong Cao, Edmund J. Moran
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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: 5744627Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula III, General Formula IV, and General Formula VI. In one embodiment, the reagents of General Formula III may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula IV. The reagent of General Formula IV may be used to form a complex with a boron compound, such as a complex shown in General Formula VI.Type: GrantFiled: August 5, 1996Date of Patent: April 28, 1998Assignees: Prolinx, Inc., SystemixInventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
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Patent number: 5734082Abstract: This invention relates to a class of aminimides structurally characterized as an acyl nitrogen-nitrogen ylide such that the acyl moiety possess the structural diversity element G, the quaternary nitrogen possess structural diversity elements E and F, and the quaternary nitrogen is bonded to a hydroxyethyl substituent, which in turn is bonded to an aminomethylene moiety that possess structural diversity elements A and B from the amino group and diversity element C from the methylene substituent, as shown below, ##STR1## wherein structural diversity element A, B, C, D, E, F and G are chosen from the set of elements consisting of substituted and unsubstituted as well as branched and straight chain alkyl, aryl, alkaryl, aralkyl, carbocyclic, heterocyclic, hydrogen, amino acid, peptide, polypeptide, protein, depsipeptide, carbohydrate derivatives, nucleotide derivatives, oligonucleotide derivatives, naturally occurring or synthetic organic structural motifs, reporter elements, organic moieties containing at leastType: GrantFiled: October 20, 1994Date of Patent: March 31, 1998Assignee: Arqule Inc.Inventors: Joseph C. Hogan, Jr., David Casebier, Paul S. Purth, Steve Gallion, Alan Kaplan
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Process for preparing benzoic acid derivative intermediates and benzothiophene pharmaceutical agents
Patent number: 5731436Abstract: Processes for producing benzothiophenes employing ethylene carbonate or propylene carbonate are provided.Type: GrantFiled: August 31, 1994Date of Patent: March 24, 1998Assignee: Eli Lilly and CompanyInventor: Douglas P. Kjell -
Patent number: 5726165Abstract: A compound of formula (I): ##STR1## or a pharmaceutically acceptable salt, or solvate thereof, wherein,R.sup.o represents an aryl group, optionally substituted;X represents O or S;R.sup.1 and R.sup.1a each independently represents hydrogen or an alkyl group;R.sup.2 represents OCH.sub.2 CO.sub.2 H, or an ester or amide thereof, or R.sup.2 represents a moiety of formula (b): ##STR2## wherein R.sup.4 represent hydrogen, alkyl, hydroxyalkyl, arylalkyl, aralkyloxyalkyl or cycloalkyl and R.sup.5 represent hydroxy, alkoxy, arylalkyloxy, hydroxyalkyloxy, alkoxyalkyloxy, arylalkoxyalkyloxy, cycloalkyloxy, hydrogen, alkyl, substituted alkyl, cycloalkyl, aryl, arylalkyl, arylalkyloxyalkyl or R.sup.5 together with OR.sup.4 represents O(CH.sub.2).sub.n O wherein n is 2, 3 or 4; andR.sup.3 represents hydrogen, halogen, alkyl or alkoxy or R.sup.3 together with R.sup.Type: GrantFiled: June 5, 1995Date of Patent: March 10, 1998Assignee: SmithKline Beecham p.l.c.Inventors: Lee James Beeley, Mervyn Thompson, David Kenneth Dean, Nikesh Rasiklal Kotecha, John Michael Berge, Robert William Ward
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Patent number: 5723489Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sup.1 to R.sup.9 are as defined herein and m is the integer 0 or 1.These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity, gastrointestinal diseases and achalasia.Type: GrantFiled: May 7, 1996Date of Patent: March 3, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Philip M. Sher, William N. Washburn, Kathleen M. Poss
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Patent number: 5714517Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.Type: GrantFiled: August 22, 1996Date of Patent: February 3, 1998Assignee: Monsanto CompanyInventor: Peter Gerrard Ruminski
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Method for lowering oxygen affinity of hemoglobin in redcell suspensions, in whole blood and in vivo
Patent number: 5661182Abstract: Drug compounds are used as allosteric modifiers of hemoglobin present in red blood cells. The compounds bind to only a single pair of symmetry related sites in the central water cavity of hemoglobin at the Lys 99.alpha., Arg 141.alpha., and Asn 108 .beta. residues. When one of the drug compounds is bound to hemoglobin, it will join three separate sub-units of the hemoglobin molecule and stabilize the hemoglobin in a lower oxygen affinity state. Because the compounds used in this method are either not bound by serum albumin or only interact to small degrees with serum albumin, the compounds are active in whole blood and in vivo. The process of allosterically modifying hemoglobin towards a low oxygen affinity state in whole blood and in vivo could be used in a wide variety of applications including in treatments for ischemia, heart disease, wound healing, Alzheimer's, depression, schizophrenia, adult respiratory distress syndrome (ARDS), etc.Type: GrantFiled: June 7, 1995Date of Patent: August 26, 1997Assignee: Virginia Commonwealth UniversityInventors: Donald J. Abraham, Claude Poyart -
Patent number: 5635534Abstract: Compounds of formula (I): ##STR1## (wherein: R.sup.0 is hydrogen, methyl or hydroxymethyl; R.sup.1 is substituted alkyl; R.sup.2 and R.sup.3 are each hydrogen, halogen, hydroxy, alkoxy, carboxy, alkoxycarbonyl, alkyl, nitro, haloalkyl, or substituted alkyl; X is oxygen or sulfur; and Ar optionally substituted phenyl or naphthyl); and pharmaceutically acceptable salts thereof have a variety of valuable pharmaceutical activities, including anti-diabetic and anti-obesity activities; in addition, they are capable of treating or preventing hyperlipemia and hyperglycemia and, by inhibiting the action of aldose reductase, they can also be effective in the treatment and prevention of complications of diabetes.Type: GrantFiled: June 7, 1995Date of Patent: June 3, 1997Assignee: Sankyo Company, LimitedInventors: Takashi Fujita, Takao Yoshioka, Horoyoshi Horikoshi, Shinji Yoshioka
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Patent number: 5631401Abstract: The present invention provides a compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof, which are useful in inhibiting protein farnesyltransferase and the farnesylation of the oncogene protein Ras or inhibiting de novo squalene production resulting in the inhibition of cholesterol biosynthesis, processes for the preparation of the compounds of the invention in addition to intermediates useful in these processes, a pharmaceutical composition, and to methods of using such compounds.Type: GrantFiled: January 24, 1995Date of Patent: May 20, 1997Assignee: Abbott LaboratoriesInventors: Herman H. Stein, William R. Baker, Anthony K. L. Fung, Saul H. Rosenberg, Todd W. Rockway, Stephen A. Fakhoury, David S. Garvey, B. Gregory Donner, William J. McClellan, Stephen J. O'Connor, Rajnandan Prasad, Wang Shen, Gerard M. Sullivan
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Patent number: 5624961Abstract: Novel benzylaminoethoxybenzene derivatives of the formula (I) ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl, a lower hydroxyalkyl, a lower alkoxyalkyl, an allyl or a benzyl; R.sup.2 is a hydrogen atom, a lower alkyl, a lower acyl, an allyl or a benzyl; R.sup.3 is a hydrogen atom, a lower alkyl, a lower alkoxyalkyl, a lower dialkylaminoalkyl or a lower acyl; and R.sup.4 is a hydrogen atom, a halogen atom, a lower alkoxy, an amino, a lower acylamino, a hydroxy, a lower acyloxy, a lower acyl, a carboxy or a lower alkoxycarbonyl, salts thereof and solvates thereof. An .alpha..sub.1 -adrenoceptor blocker obtained from this compound has a strong .alpha..sub.1 -adrenoceptor blocking effect and causes less side effects such as orthostatic hypotension.Type: GrantFiled: December 11, 1995Date of Patent: April 29, 1997Assignee: Japan Tobacco Inc.Inventors: Masakazu Ban, Kiyotaka Shinoda, Mitsuru Takahashi, Shuhei Deguchi, Hiroaki Taguchi, Takeo Katsushima
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Patent number: 5606095Abstract: 2-Aminooxymethylenephenylacetic acid ester derivatives of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are hydrogen, halogen, hydroxy, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylcarbonyl, phenoxy, nitro or cyano, or Z.sub.1 and Z.sub.2, together with the linking phenyl radical, are naphthalene or hydrogenated naphthalene, and R.sub.3 is hydrogen or C.sub.1 -C.sub.12 alkyl. The compounds of this invention may be used as the free base or as a protic acid salt and are important intermediates for the manufacture of microbicides for plant protection.Type: GrantFiled: June 5, 1995Date of Patent: February 25, 1997Assignee: Ciba-Geigy CorporationInventors: Albert Pfiffner, Stephan Trah, Hugo Ziegler
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Patent number: 5597943Abstract: The present invention relates to the new thielocin derivatives, which exhibit phospholipase A.sub.2 inhibitory activity of the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, and R.sup.8 are independently hydrogen, lower alkyl, lower alkoxy, hydroxy, or halogen;E.sub.1 and E.sub.2 are independently hydrogen, or an ester residue;m and n are independently an integer of 0 to 4;--Y-- is a bivalent group which is selected from the group consisiting of the following radicals: ##STR2## or the salts thereof.Type: GrantFiled: December 13, 1995Date of Patent: January 28, 1997Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Shigeru Matsutani, Tadashi Yoshida, Kazushige Tanaka, Yasuhiko Fujii, Kazuhiro Shirahase
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Patent number: 5596009Abstract: A fused benzeneoxyacetic acid derivative of the formula (I): ##STR1## A is --COW, --NR.sup.4 --Y or --Z--NR.sup.4 --CONR.sup.2 R.sup.3 ; and salts thereof possess an agonistic on PGI.sub.2 receptor, so it is useful for prevention and/or treatment of thrombosis, arteriosclerosis, ischemic heart diseases, gastric ulcer and hypertention.Type: GrantFiled: May 19, 1994Date of Patent: January 21, 1997Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Nobuyuki Hamanaka, Kanji Takahashi, Hidekado Tokumoto
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Patent number: 5576332Abstract: New soft .beta.-adrenergic blocking agents, useful in the treatment or prevention of cardiovascular disorders and in the treatment of glaucoma, have the formula ##STR1## wherein n is an integer from 0 to 10; R is C.sub.6 -C.sub.12 cycloalkyl-C.sub.p H.sub.2p --, C.sub.6 -C.sub.18 polycycloalkyl-C.sub.p H.sub.2p --, C.sub.6 -C.sub.18 polycycloalkenyl-C.sub.p H.sub.2p -- or C.sub.6 -C.sub.12 cycloalkenyl-C.sub.p H.sub.2p -- (wherein p is 0, 1, 2 or 3), or together with the adjacent ##STR2## group represents a variety of other complex ester groupings; R.sub.1 is C.sub.1 -C.sub.7 alkyl; and Ar is a divalent radical containing at least one aromatic nucleus. The corresponding pharmaceutically acceptable acid addition salts are also described.Type: GrantFiled: May 31, 1995Date of Patent: November 19, 1996Inventor: Nicholas S. Bodor
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Patent number: 5547983Abstract: Aromatic bicyclic compounds of formula (I) ##STR1## where R.sub.1 is specifically --H, CH.sub.3, --CH.sub.2 OH, --OH, --CHO, --CONH.sub.2, --COOH, --COOalkyl, --SH, S-alkyl, etc. . . . ; R.sub.2 is H; R.sub.3 is H, aryl, aralkyl or lower alkyl optionally substituted by a hydroxyl, a lower alkoxy or a --CO--R.sub.12, R.sub.12 being specifically H, lower alkyl, hydroxyl, lower alkoxy, or R.sub.2 and R.sub.3 together form a naphthalene ring with the benzene ring; R.sub.4 is a linear branched or unbranched alkyl having 1 to 15 carbon atoms or a cycloaliphatic radical; R.sub.5 represents specifically --(CH.sub.2).sub.n --R.sub.13, --CH.dbd.CH--(CH.sub.2).sub.n --R.sub.13, n being 0 or 1 to 6, R.sub.13 representing --COR.sub.15, monohydroxyalkyl, polyhydroxyalkyl, epoxy lower alkyl or --O--CO--R.sub.16, R.sub.15 representing specifically --OH, --Oalkyl, --Oaryl, R.sub.16 being specifically H, lower alkyl, aryl, or aralkyl; R.sub.6 and R.sub.7 are H, a halogen, lower alkyl or --OR.sub.Type: GrantFiled: August 22, 1994Date of Patent: August 20, 1996Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)Inventor: Bruno Charpentier
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Patent number: 5545745Abstract: The invention relates to a method for producing albuterol by the resolution of a mixture of enantiomers of methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-(phenylmethoxy)benzoate or .alpha.-[[(1,1-dimethylethyl)amino]methyl]-4-(phenylmethoxy)-1,3-benzenedi methanol using a chiral acid such as (+/-) di-toluoyltartaric acid or (+/-) di-benzoyltartaric acid.Type: GrantFiled: January 20, 1995Date of Patent: August 13, 1996Assignee: Sepracor, Inc.Inventors: Yun Gao, Charles M. Zepp
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Patent number: 5543433Abstract: Compounds of the formula I ##STR1## where X is hydrogen, halogen, alkyl, alkoxy, trifluoromethyl, cyano or nitro,Y is an amino, methylamino or dimethylamino group,Z is a group CHCH.sub.3, CHOCH.sub.3 or NOCH.sub.3,R is hydrogen or alkyl,A is hydrogen, alkyl, haloalkyl or cycloalkyl,B is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl or the group ##STR2## where W is hydrogen, alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, unsubstituted or substituted aryl or heteroaryl, unsubstituted or substituted aryloxy, arylthio, arylamino or aryl-N-(C.sub.1 -C.sub.6 -alkyl)amino, heteroaryloxy, heteroarylthio, heteroarylamino or heteroaryl-N-(alkyl)amino orA and B, together with the C atom whose substituents they are, are an isocyclic or heterocyclic ring which can also be quinonoid,and fungicides containing these compounds.Type: GrantFiled: June 3, 1994Date of Patent: August 6, 1996Assignee: BASF AktiengesellschaftInventors: Reinhard Doetzer, Hubert Sauter, Herbert Bayer, Franz Roehl, Gisela Lorenz, Eberhard Ammermann, Horst Wingert
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Patent number: 5523302Abstract: This invention relates to novel compounds containing basic and acidic termini, pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of platelet aggregation, as thrombolytics, and/or for the treatment of thromboembolic disorders.Type: GrantFiled: November 24, 1993Date of Patent: June 4, 1996Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Gary A. Cain, Charles J. Eyermann