The 4-position Of The Hetero Ring Is Unsubstituted Or Alkyl Substituted Only Patents (Class 540/362)
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Patent number: 5300509Abstract: Compounds of formula I, and pharmaceutically acceptable salts thereof, ##STR1## in which R1 is hydrogen (1-6C)alkyl or (1-4C)alkanoyl;A is --N.dbd.CQ--O--, N.dbd.CQ--NR.sup.8 --, --N.dbd.CQ--CH.dbd.N--or --N.dbd.CH--CQ.dbd.N--;Q is 2-furyl;R.sup.8 is hydrogen or C1-4C)alkyl;and R.sup.2 has any of the meanings given in the specification, processes for preparing the compounds and pharmaceutical compositions containing them. The compounds are useful as adenosine antagonists.Type: GrantFiled: November 20, 1992Date of Patent: April 5, 1994Assignee: Imperial Chemical Industries PLCInventors: Michael H. Block, Alison Harrison, Rodney B. Hargreaves
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Patent number: 5296595Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes a two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation.Type: GrantFiled: September 24, 1992Date of Patent: March 22, 1994Assignee: Research Corporation TechnologiesInventor: Michael P. Doyle
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Patent number: 5284857Abstract: Substituted thienopyrans and processes for preparing the thienopyrans are disclosed. The thienopyrans are useful as antihypertensive agents; antianginals are peripheral antivasoconstrictive agents.Type: GrantFiled: December 21, 1990Date of Patent: February 8, 1994Assignee: Ortho Pharmaceutical CorporationInventors: Jeffery B. Press, Pauline Sanfilippo, James J. McNally, Robert Falotico
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Patent number: 5250677Abstract: The present invention relates to new 3-guanidinoalkyl-2-azetidinones of the formula ##STR1## wherein: U and W can be the same or different and are selected from the group consisting of hydrogen and an amino protecting group;n is 1 to 3;X is a member selected from the group consisting of hydrogen, trialkylsilyl, arylsulfonyl, amino substituted arylsulfonyl, alkylsulfonyl, arylaminocarbonyl, alkylcarbonyl and arylcarbonyl; andY is a member selected from the group consisting of hydrogen, arylalkenyl, arylalkyl, formyl, carboxy, alkoxycarbonyl, acyloxy, arylthio, arylsulfinyl, arylsulfonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, arylaminocarbonyl, the radical ##STR2## in which R is hydrogen, alkyl or arylalkyl, and the radical ##STR3## in which m is 1 to 3 and R' is hydrogen or --CO.sub.2 R" wherein R" is hydrogen, alkyl or arylalkyl.The novel azetidinones of the present invention exhibit anti-thrombin and anti-trypsin activities and are thus useful in controlling blood coagulation and treating pancreatitis.Type: GrantFiled: October 6, 1992Date of Patent: October 5, 1993Assignee: Bristol-Myers Squibb CompanyInventor: William T. Han
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Patent number: 5250676Abstract: Provided is a process for diastereoselectively preparing compounds of the formula ##STR1## which includes the step of subjecting a compound of the formula ##STR2## to a salt whose anion is a nucleophilic base whose conjugate acid has a pKa in the range of between about -7 to about 14, or a silylated derivative of the salt; whereinR.sub.1 is said nucleophile;R is hydrogen, or protected amino,R.sub.2 is R.sub.4 as defined herein below;R.sub.3 is a leaving group; andR.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, or a group of the formula--CH.sub.2 --CH.sub.2 --R.sub.6whereinR.sub.6 is 2-furyl, naphthyl, phenyl, phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido; orR.sub.6 is a group of the formula--COOR.sub.7or--COSR.sub.7in whichR.sub.7 is selected from C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, benzyl, phenyl, or benzyl or phenyl substituted with 1, 2 or 3 substituents selected from C.sub.Type: GrantFiled: March 23, 1992Date of Patent: October 5, 1993Assignee: University of Notre Dame du LacInventors: Catherine M. Gasparski, Marvin J. Miller, Min Teng
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Patent number: 5241064Abstract: Preparation of optically active 3-substituted azetidinones of the formula (I) ##STR1## in which R.sup.1 is a hydroxy-protective group wherein an allylic alcohol of the formula (II) ##STR2## is acylated, then subjected to asymmetric enzymatic hydrolysis yielding the R-allylic alcohol. The hydroxyl group is protected and then stereoselectively reacted with an amine which is subsequently cyclized to yield the desired 3-substituted azetidinone. Two new species of microorganisms have been isolated, Pimelobacter sp. No. 1254 and Bacillus megaterium No. 1253 which exhibit stereoselective esterase activity.Type: GrantFiled: September 24, 1990Date of Patent: August 31, 1993Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Masayoshi Murata, Toshiyuki Chiba, Fumiyuki Shirai, Kenichi Washizuka, Motohiro Hino
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Patent number: 5229381Abstract: New substituted azetidinones of the general formula (A') which have been found to be potent elastase inhibitors and thereby useful anti-inflammatory and antidegenerative agents are described.Type: GrantFiled: September 20, 1991Date of Patent: July 20, 1993Assignee: Merck & Co., Inc.Inventors: James B. Doherty, Conrad P. Dorn, Paul E. Finke, William K. Hagmann, Malcolm MacCoss, Shrenik K. Shah
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Patent number: 5204461Abstract: A process for preparing (1'R,3S)-3-(1'-hydroxyethyl)-azetidin-2-one or a derivative thereof represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a hydroxyl-protective group, is disclosed, comprising reacting (2S,3R)-2-aminomethyl-3-hydroxybutyric acid or a derivative thereof represented by formula (II): ##STR2## wherein R.sup.1 is as defined above, with a sulfenamide represented by formula (III): ##STR3## wherein R.sup.2 represents ##STR4## and R.sup.3 and R.sup.4 each represent a hydrogen atom or a cyclic or acyclic hydrocarbon group, provided that they do not simultaneously represent a hydrogen atom, or R.sup.3 and R.sup.4 are taken together with the adjacent nitrogen atom to form a heterocyclic group, and triphenylphosphine. The reaction yield is high, and the sulfenamide (III) used as a lactamization reagent is cheap and can be recovered after the reaction.Type: GrantFiled: November 8, 1991Date of Patent: April 20, 1993Assignee: Takasago International CorporationInventors: Toshiyuki Murayama, Takashi Miura, Toyohiko Kobayashi
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Patent number: 5202433Abstract: A polysaccharide derivative prepared by replacing a part or the whole of hydrogen atoms of hydroxyl and/or amino groups of a polysaccharide with one or more atomic groups represented by the following formula (1), (2) or (3) is new and useful for the separation of optical isomers: ##STR1## wherein the number of carbon atoms constituting R is 1 to 30 and R is a group having at least one asymmetric center.Type: GrantFiled: January 18, 1991Date of Patent: April 13, 1993Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshio Okamoto, Koichi Hatada
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Patent number: 5196415Abstract: This invention is in the field of clinical neurology and relates specifically to compounds, compositions and methods for treatment of patients with generalized epilepsy or partial (symptomatic) epilepsy using compounds of the formula: ##STR1## This invention also relates to compounds, compositions and methods of treatment for drug craving in patients addicted to cocaine.Type: GrantFiled: January 29, 1992Date of Patent: March 23, 1993Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: James A. Monn, Andrew Thurkauf, Shunichi Yamaguchi, Michael A. Rogawski, Kenner C. Rice, Mariena V. Mattson, Arthur E. Jacobson
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Patent number: 5175283Abstract: The present invention relates to new 3-guanidinoalkyl-2-azetidinones of the formula ##STR1## wherein: U and W can be the same or different and are selected from the group consisting of hydrogen and an amino protecting group;n is 1 to 3;X is a member selected from the group consisting of hydrogen, trialkylsilyl, arylsulfonyl, amino substituted arylsulfonyl, alkylsulfonyl, arylaminocarbonyl, alkylcarbonyl and arylcarbonyl; andY is a member selected from the group consisting of hydrogen, arylalkenyl, arylalkyl, formyl, carboxy, alkoxycarbonyl, acyloxy, arylthio, arylsulfinyl, arylsulfonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, arylaminocarbonyl, the radical ##STR2## in which R is hydrogen, alkyl or arylalkyl, and the radical ##STR3## in which m is 1 to 3 and R' is hydrogen or --CO.sub.2 R" wherein R" is hydrogen, alkyl or arylalkyl.The novel azetidinones of the present invention exhibit anti-thrombin and anti-trypsin activities and are thus useful in controlling blood coagulation and treating pancreatitis.Type: GrantFiled: February 11, 1992Date of Patent: December 29, 1992Assignee: Bristol-Myers Squibb CompanyInventor: William T. Han
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Patent number: 5116971Abstract: The invention relates to new 1,4-diazepines of the general formula ##STR1## in which R.sub.1, R.sub.2 R.sub.3, X and A have the meaning indicated in the specification.The new compounds are intended for use for the treatment of pathological states and diseases in which PAF (platelet activating factor) is involved.Type: GrantFiled: September 19, 1990Date of Patent: May 26, 1992Assignee: Boehringer Ingelheim KGInventors: Albrecht Harreus, Karl-Heinz Weber, Werner Stransky, Gerhard Walther, Gojko Muacevic, Jorge C. Stenzel, Wolf-Dietrich Bechtel
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Patent number: 5112966Abstract: A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a lower alkyl group or a 1-hydroxy(lower)alkyl group wherein the hydroxyl group is optionally protected, R.sub.2 is a hydrogen atom or a protective group for the nitrogen atom and R.sub.3 is a methyl group, a halomethyl group, a hydroxymethyl group, a protected hydroxymethyl group, a formyl group, a carboxyl group, a lower alkoxycarbonyl group or an ar(lower)alkoxycarbonyl group wherein the aryl group is optionally substituted, or R.sub.2 and R.sub.3 are combined together to form an oxaalkylene group and, when taken together with one nitrogen atom and two carbon atoms adjacent thereto, they represent a six-membered cyclic aminoacetal group, which is useful as a valuable intermediate in the stereospecific production of 1-methylcarbapenem compounds.Type: GrantFiled: October 31, 1985Date of Patent: May 12, 1992Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Haruki Matsumura, Tsuneo Yano, Akira Sasaki, Shinzi Takata
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Patent number: 5106475Abstract: A process for preparing 3-4-cis-.beta.,.beta.-(4)-substituted and 3-4-trans,.beta.,.alpha.-(4)-substituted azetidinones is provided. Also provided are novel 4,4-disubstituted azetidinones.Type: GrantFiled: October 16, 1990Date of Patent: April 21, 1992Assignee: Eli Lilly and CompanyInventors: John M. Morin, Jr., Robert J. Ternansky, David A. Hall
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Patent number: 5037819Abstract: The present invention relates to new 3-guanidinoalkyl-2-azetidinones of the formula ##STR1## wherein: U and W can be the same or different and are selected from the group consisting of hydrogen and an amino protecting group;n is 1 to 3;X is a member selected from the group consisting of hydrogen, trialkylsilyl, arylsulfonyl, amino substituted arylsulfonyl, alkylsulfonyl, arylaminocarbonyl, alkylcarbonyl and arylcarbonyl; andY is a member selected from the group consisting of hydrogen, arylalkenyl, arylalkyl, formyl, carboxy, alkoxycarbonyl, acyloxy, arylthio, arylsulfinyl, arylsulfonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, arylaminocarbonyl, the radical ##STR2## in which R is hydrogen, alkyl or arylalkyl, and the radical ##STR3## in which m is 1 to 3 and R' is hydrogen or --CO.sub.2 R" wherein R" is hydrogen, alkyl or arylalkyl.The novel azetidinones of the present invention exhibit anti-thrombin and anti-trypsin activities and are thus useful in controlling blood coagulation and treating pancreatitis.Type: GrantFiled: June 4, 1990Date of Patent: August 6, 1991Assignee: Bristol-Myers Squibb CompanyInventor: William T. Han
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Patent number: 4994450Abstract: A compound, or a solvate or salt thereof, of formula (I) ##STR1## in which: R.sub.1 and R.sub.2 are independently hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.3-6 cycloalkyl or C.sub.4-12 cycloalkylalkyl groups, or together form a C.sub.2-8 branched or linear polymethylene or C.sub.2-6 alkenylene group optionally substituted with a hetero-atom, provided that R.sub.1 and R.sub.2 are not simultaneously hydrogen;R.sub.3 is hydrogen, C.sub.1-6 alkyl, preferably methyl or ethyl, or phenyl, or R.sub.3 together with R.sub.1 form a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- group;p is 1, 2, 3 or 4, andR is a group of formula (II) ##STR2## in which the group --(CHR.sub.4).sub.n --X-- is in the meta- or para-position with respect to YR.sub.5 or R.sub.6, R.sub.4 is hydrogen or C.sub.1-6 alkyl, preferably hydrogen;n is 0, 1 or 2, preferably 1;X is a direct bond, or O, S or NR.sub.a in which R.sub.a is hydrogen or C.sub.1-6 alkyl, and is preferably a direct bond;Y is >C.dbd.O, >CHOH, --S.dbd.O or --SO.Type: GrantFiled: February 10, 1989Date of Patent: February 19, 1991Assignee: Dr. Lo. Zambeletti S.p.A.Inventors: Vittorio Vecchietti, Antonio Giordani
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Patent number: 4992545Abstract: A process for preparing 3-4-cis-.beta.,.beta.-(4)-substituted and 3-4-trans,.beta.,.alpha.- (4)-substituted azetidinones is provided. Also provided are novel 4,4-disubstituted azetidinones.Type: GrantFiled: September 20, 1989Date of Patent: February 12, 1991Assignee: Eli Lilly and CompanyInventors: David A. Hall, deceased, John M. Morin, Jr., Robert J. Ternansky
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Patent number: 4992435Abstract: Substituted thienopyrans and processes for preparing the thienopyrans are disclosed. The thienopyrans are useful as antihypertensive agents; antianginals are peripheral antivasoconstrictive agents.Type: GrantFiled: September 23, 1988Date of Patent: February 12, 1991Assignee: Ortho Pharmaceutical CorporationInventors: Jeffery B. Press, Pauline Sanfilippo, James J. McNally, Robert Falotico
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Patent number: 4981992Abstract: A process for preparing an optically active 3-hydroxybutanoic acid represented by formula (I): ##STR1## wherein: R.sup.1 represents a protective group of carboxylic acid, andR.sup.2 represents a hydrogen atom; a lower alkyl group which may be substituted with a halogen atom; a lower alkoxy group; a phenyl group which may be substituted with a lower alkyl group or a lower alkoxy group; or a benzyloxy group which may be substituted with a lower alkyl group or a lower alkoxy group,is disclosed, comprising asymmetrically hydrogenating a 3-oxobutanoic acid ester represented by formula (II): ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst. The compound of formula (I) which is useful for synthesizing a 4-acetoxyazetidin-2-one derivative, a useful intermediate for obtaining penem antibiotics, can be prepared economically.Type: GrantFiled: November 14, 1989Date of Patent: January 1, 1991Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Yoshiki Okeda, Hiroyuki Nagashima, Hidonori Kumobayashi
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Patent number: 4939133Abstract: The present invention relates to novel N-substituted 2-hydroxybenzamide and N-substituted 2-hydroxy-.alpha.-oxo-benezene acetamide compounds pharmaceutical compositions, and methods of use for therefore for the treatment of diseases in which products having lipoxygenase enzyme activity contribute to the pathological condition. Selected novel intermediates are also the present invention.Type: GrantFiled: October 1, 1985Date of Patent: July 3, 1990Assignee: Warner-Lambert CompanyInventors: David T. Connor, Daniel L. Flynn, Wiaczeslaw A. Cetenko, Jagadish C. Sircar, Charles F. Schwender, Elizabeth A. Johnson, Roderick J. Sorenson, Paul C. Unangst
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Patent number: 4886890Abstract: This invention relates to quaternary compounds having the formula ##STR1## wherein W.sup.- is an anion; m and n are integers having a value of from 1 to 4; R is alkylene having from 3 to 8 carbon atoms; R.sub.1 is a radical having from 8 to 25 carbon atoms and is selected from the group of alkyl, alkenyl and alkoxy alkylene and each of R.sub.2, R.sub.3 and R.sub.4 is a radical having from 1 to 25 carbon atoms and is alkyl, alkoxy or ##STR2## where p has a value of from 1 to 4 and X is hydrogen or methyl. The invention also relates to the preparation and use of said diquaternized compounds.Type: GrantFiled: September 29, 1988Date of Patent: December 12, 1989Assignee: GAF CorporationInventors: Ratan K. Chaudhuri, David J. Tracy, Robert B. Login
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Patent number: 4834846Abstract: This invention relates to a process for preparing .beta.-lactams by electrochemically deblocking N-substituting .beta.-lactams using anodic oxidation.Type: GrantFiled: December 7, 1987Date of Patent: May 30, 1989Assignee: Merck & Co., Inc.Inventors: Newton L. Abramson, Sandor Karady, Edward G. Corley, Leonard M. Weinstock
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Patent number: 4795809Abstract: A compound having the formula (I): ##STR1## is described, together with salts thereof and an enzymatic process for converting such compounds into clavulanic acid.A process for the preparation of the compound of formula (I) and its salts is disclosed, together with intermediates for use therein. This process involves the use of a novel enzyme system to effect the desired cyclization, which enzyme system is preferably derived from a micro-organism, in particular a species of Streptomyces.Type: GrantFiled: August 27, 1986Date of Patent: January 3, 1989Assignee: Beecham Group plcInventors: Stefan R. Woroniecki, Stephen W. Elson, Keith H. Baggaley
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Patent number: 4719207Abstract: Substituted azetidinone compounds are provided which have the formula: ##STR1## wherein one of R.sup.1 and R.sup.2 represents a substituted lower alkyl group, an azido group, an amino group, a lower acylamino group, a mercapto group or a lower alkylthio group and the other represents a hydrogen group, or, both represent hydrogen atoms or lower alkyl groups; R.sup.3 represents a hydrogen atom or a group shown by formula: ##STR2## (wherein X represents ##STR3## (wherein R.sup.5 represents a hydrogen atom or a lower alkyl group) and Y represents a hydroxy group, a lower alkoxy group, an amino group, a mono- or di-lower alkylamino group); R.sup.4 represents a hydrogen atom, a substituted or unsubstituted lower alkyl group or a group shown by formula: --CH.sub.2 CO--A (wherein A represents an amino group or a group shown by formula: ##STR4## (wherein X and Y are as defined above), provided that when R.sup.1 and R.sup.2 are both hydrogen atoms, at least R.sup.Type: GrantFiled: June 20, 1985Date of Patent: January 12, 1988Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Toshinari Tamura, Makoto Yoshida, Shin-ichi Tsukamoto, Hidenori Iwamoto, Minoru Yamamoto, Soichi Kagami
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Patent number: 4683303Abstract: Novel process for the preparation of azetidin-2-ones of the formula ##STR1## wherein R.sup.1 and R.sup.2 independently from each other are hydrogen, or an organic group linked to the ring carbon via a carbon atom, a nitrogen atom or an oxygen atom, characterized in that a corresponding 4-acyloxyazetidin-2-one, which is substituted by a group --O--CO--R.sup.3 at the 4-position, wherein R.sup.3 is hydrogen or an organic radical stable at the reaction conditions, is reacted with a complex metal hydride comprising reactive hydride ions, such as, lithium borohydride, sodium borohydride, potassium borohydride, zinc borohydride or tetraorganoammonium borohydride.Type: GrantFiled: October 30, 1984Date of Patent: July 28, 1987Inventor: Hans R. Pfaendler
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Patent number: 4680391Abstract: New substituted azetidinones are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.Type: GrantFiled: April 10, 1985Date of Patent: July 14, 1987Assignee: Merck & Co., Inc.Inventors: Raymond A. Firestone, Peter L. Barker
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Patent number: 4652563Abstract: This invention relates to dihydropyridazinone compounds having a cyclopropylmethoxyethyl group in the 6-substituent. These compounds are vasodilators and .beta.-adrenoceptor antagonists. A particular compound of the invention is 6-[4-[3-[2-hydroxy-3-[4-(2-(cyclopropylmethoxy) ethyl)phenoxy]propylamino]propionamido]phenyl]-5-methyl-4,5-dihydro-3 (2H)-pyridazinone.Type: GrantFiled: May 16, 1985Date of Patent: March 24, 1987Assignee: Smith Kline & French Laboratories Ltd.Inventor: Robert A. Slater
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Patent number: 4629495Abstract: Herbicidal compounds of the formula: ##STR1## wherein A represents R.sup.1 R.sup.2 N-- (wherein R.sup.1 represents C.sub.1-8 alkyl or C.sub.2-8 alkenyl or alkynyl unsubstituted or substituted by CN, OH, C.sub.1-6 alkoxy, carboxy, C.sub.2-9 alkoxycarbonyl, aminocarbonyl optionally substituted by C.sub.1-8 alkyl or C.sub.2-8 alkenyl, C.sub.1-8 alkoxyaminocarbonyl, C.sub.1-8 alkanesulphonamidocarbonyl, --C(.dbd.O)Het, where Het represents a nitrogen-containing heterocyclic group, or one or more halogen atoms or R.sup.1 represents C.sub.3-6 cycloalkyl optionally substituted by C.sub.1-4 alkyl and R.sup.2 represents H or R.sup.1, or R.sup.1 represents C.sub.1-4 alkylthio and R.sup.2 represents H, or A represents R.sup.p (R.sup.q)--C.dbd.N-- (wherein R.sup.p represents C.sub.1-4 alkoxy or amino substituted by one or two C.sub.1-4 alkyl groups and R.sup.q represents H or C.sub.1-4 alkyl) or A represents 2-oxo-azetidin-1-yl, 2-oxo-pyrrolidin-1-yl or 2-oxo-piperidin-1-yl optionally substituted by C.sub.Type: GrantFiled: July 13, 1983Date of Patent: December 16, 1986Assignee: May & Baker LimitedInventors: Leslie R. Hatton, Edgar W. Parnell, David A. Roberts