4- Or 5-position Substituent Contains Chalcogen Patents (Class 548/232)
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Patent number: 5849921Abstract: Angiotensin-II antagonists of the formula ##STR1## wherein R.sub.1 is, other than hydrogen and, inter alia, halogen, lower alkyl or cycloalkyl; R.sub.2 is, inter alia, optionally substituted benzimidazol-2-yl, 5,6,7,8-tetrahydro-imidazo?1,2-a!pyridin-2-yl, butanesultam-1-yl, imidazol-4-yl, and tetrahydobenzimidazol-2-yl; R.sub.3 is, inter alia, lower alkyl; and, R.sub.4 is an acidic group, such as carboxyl or tetrazolyl. An exemplary compound is: 4'-?(2-ethyl-4-methyl-6-(5,6,7,8-tetrahydroimidazo?1,2-a!pyridin-2-yl)-ben zimidazol-1-yl)-methyl!-biphenyl-2-carboxylic acid.Type: GrantFiled: June 2, 1995Date of Patent: December 15, 1998Assignee: Astra AktiebolagInventors: Robin Bernad Boar, Alan John Cross, Duncan Alastair Gray, Richard Alfred Green
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Patent number: 5750696Abstract: Dioxacycloalkane compounds of the formula ?1! ##STR1## wherein A is ##STR2## wherein W is ##STR3## X is --CO-- or --SO.sub.2 --; Y is --CH.sub.2 --, --O-- or --NR.sup.25 --; and R.sup.1 is an aralkyl which may be substituted by lower alkoxy;R.sup.2 is a hydrogen atom or a lower alkyl;R.sup.3 is --(CH.sub.2)d-SR.sup.26 or ##STR4## R.sup.4 and R.sup.5 are each a hydrogen atom or a lower alkyl; and E is --C(R.sup.29)(R.sup.30)-- or --CH.sub.2 CH.sub.2 --, pharmaceutically acceptable salts thereof, intermediates for producing said compounds, and methods for producing said intermediates. The compounds of the formula ?1! have a strong inhibitory activity against renin and show continuous hypotensive action by oral administration. They are useful as hypotensive agents or therapeutic agents for heart failure.Type: GrantFiled: February 21, 1995Date of Patent: May 12, 1998Assignee: Japan Tobacco Inc.Inventors: Saizo Shibata, Yasuki Yamada, Koji Ando, Kiyoshi Fukui, Ikuro Nakamura, Itsuo Uchida
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Patent number: 5747501Abstract: Compounds of the formula ##STR1## where W is ##STR2## n is 0, 1, or 2; m is 0, 1, 2, or 3: Y and G are each independently oxygen or sulfur; Z is --O--, --S--, --NH, or --CH.sub.2 ; R.sub.1 is hydrogen, C.sub.1 to C.sub.8 alkyl, substituted C.sub.1 to C.sub.8 alkyl substituted with one hydroxy, C.sub.3 to C.sub.8 alkenyl, C.sub.3 to C.sub.8 alkynyl, aryl, C.sub.1 to C.sub.3 alkylaryl, C.sub.1 to C.sub.3 alkylheteroaryl, or --Q--R.sub.4 ; R.sub.2 and R.sub.3 are each independently hydrogen, C.sub.1 to C.sub.6 alkyl, aryl, C.sub.1 to C.sub.3 alkylaryl, or C.sub.1 to C.sub.3 alkylheteroaryl; R.sub.4 is cyano, trifluoromethyl, --COR.sub.9, --CO.sub.2 R.sub.9, --CONR.sub.9 R.sub.10, --OR.sub.9, --SO.sub.2 NR.sub.9 R.sub.10, or --S(O).sub.q R.sub.9 ; R.sub.9 and R.sub.10 are each independently hydrogen, C.sub.1 to C.sub.8 alkyl, C.sub.1 to C.sub.3 alkylaryl, aryl, or R.sub.9 and R.sub.Type: GrantFiled: September 16, 1994Date of Patent: May 5, 1998Assignee: Pfizer, Inc.Inventors: John Eugene Macor, Martin James Wythes
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Patent number: 5744611Abstract: A process is disclosed for reducing amino acids and derivatives thereof Compounds of formula (I), in which n=0 or 1 and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the meanings given in the description, are reduced to the corresponding amino alcohols of formula (II): the formula (I) compounds are converted in a first step, in at least one alcohol and with the addition of acid and heat to an ester, this process producing a reaction mixture containing the ester; the ester is converted in a second reaction step with alkali or alkaline earth borohydride to compounds of formula II. By specifying that the second step be carried out without isolating the ester from the reaction mixture and by using alkali or alkaline earth borohydrides which are not activated, the invention facilitates the production from amino acids and their derivatives of the correponding alcohols in a simple "single vessel" process, with high yields and in such a way as to preserve a given centre of chirality.Type: GrantFiled: March 3, 1997Date of Patent: April 28, 1998Assignees: Degussa Aktiengesellschaft, Hoppman-La Rouche AGInventors: Matthias Kottenhahn, Karlheinz Drauz, Hans Hilpert
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Patent number: 5744630Abstract: The present invention has for its object to provide an efficient and economical method for producing an 3-amino-2-hydroxy-1-propanol derivative and an oxazolidinone derivative derived therefrom, both of which are of use as intermediates for the production of drugs including HIV protease inhibitors.The invention relates to a method for producing an 3-amino-2-hydroxy-1-propanol derivative of general formula (2) ##STR1## (wherein R.sup.1 represents alkyl, aralkyl or aryl; R.sup.2 and R.sup.3 independently represent hydrogen or an amino-protecting group, provided, however, that both R.sup.2 and R.sup.3 are not concurrently hydrogen) and an oxazolidinone derivative derived therefrom.Type: GrantFiled: July 18, 1995Date of Patent: April 28, 1998Assignee: Kaneka CorporationInventors: Kenji Inoue, Hiroshi Awaji, Satomi Takahashi
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Patent number: 5698574Abstract: The present invention relates to 5-membered heteroaryl-oxazolidinones, to processes for their preparation and to their use as medicaments, in particular as antibacterial medicaments.Type: GrantFiled: July 17, 1995Date of Patent: December 16, 1997Assignee: Bayer AktiengesellschaftInventors: Bernd Riedl, Dieter Habich, Andreas Stolle, Hanno Wild, Rainer Endermann, Klaus Dieter Bremm, Hein-Peter Kroll, Harald Labischinski, Klaus Schaller, Hans-Otto Werling
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Patent number: 5684198Abstract: Amides having formula I: ##STR1## wherein E, X, R.sup.2 and R.sup.3 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolysable esters thereof,which are useful in the treatment of urinary incontinence. Further provided are processes for preparing the aides and pharmaceutical compositions containing them.Type: GrantFiled: August 23, 1996Date of Patent: November 4, 1997Assignee: Imperial Chemical Industries, PLCInventors: Keith Russell, Cyrus John Ohnmacht, Keith Hopkinson Gibson
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Patent number: 5654428Abstract: The present invention discloses novel substituted aryl- and heteroarylphenyloxazolidinones which are useful as anti-bacterial agents. More specifically, the substituted aryl- and heteroarylphenyloxazolidinones of the invention are characterized by oxazolidinones having aryl or heteroaryl group at the p-position of the 3-phenyl ring and additional substitutions at the m-position(s) of the 3-phenyl ring. A compound representative of this new class of oxazolidinones is (.+-.)-5-(acetamidomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolid inone.Type: GrantFiled: June 6, 1995Date of Patent: August 5, 1997Assignee: Pharmacia & Upjohn CompanyInventors: Michael R. Barbachyn, Steven J. Brickner
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Patent number: 5633272Abstract: A class of substituted isoxazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II ##STR1## wherein R.sup.1 is selected from hydroxyl, lower alkyl, carboxyl, lower carboxyalkyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower aralkyl, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower haloalkyl, lower hydroxylalkyl, cycloalkyl, cycloalkylalkyl, and aralkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, aryl, and heteroaryl; wherein R.sup.Type: GrantFiled: June 7, 1995Date of Patent: May 27, 1997Inventors: John J. Talley, David L. Brown, Srinivasan Nagarajan, Jeffery S. Carter, Richard M. Weier, Michael A. Stealey, Paul W. Collins, Roland S. Rogers, deceased, Karen Seibert
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Patent number: 5574055Abstract: The present invention relates to compounds of the formula: ##STR1## wherein R is H or alkyl;Y.sup.1 is --CH.dbd. or --N.dbd.; andY.sup.2 --CH.dbd., --C(OH).dbd., --C(NO.sub.2).dbd., --C(NH.sub.2).dbd., --C(Hal).dbd., --N.dbd.;X is cycloalkenyl; bicyclo[2.2.1]hept-2-yl, optionally substituted by phenyl-2-oxo-5 -methoxymethyl-oxazolidinyl; bicyclo[2.2.1]-hept-5 -en-2-yl; adamantyl; or cycloalkyl or piperidinyl, optionally substituted by amino, alkyl, --CN, oxo hydroxyimino, ethylenedioxyor by --OR.sup.1,R.sup.1 is --CH(C.sub.6 H.sub.5).sub.2, --(CH.sub.2).sub.n C.sub.6 H.sub.5, alkyl, H, --(CH.sub.2).sub.n NHCOCH.sub.3, --(CH.sub.2).sub.n NH.sub.2, --(CH.sub.2).sub.n CN, --(CH.sub.2).sub.n SCH.sub.3 --(CH.sub.2).sub.n SO.sub.2 CH.sub.3, --CO-lower-alkyl, --COC.sub.6 H.sub.5, optionally substituted by oxazolidine;or by .dbd.CR.sup.2 R.sup.3,R.sup.2 is alkylR.sup.3 is H, --CN, alkyl, phenyl or COO-alkyl;or by --(CH.sub.2).sub.n R.sup.4R.sup.4 is --CN, amino, --NHCOCH.sub.3, --COC.sub.6 H.sub.Type: GrantFiled: December 2, 1994Date of Patent: November 12, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Janos Borgulya, Hans Bruderer, Roland Jakob-Roetne, Stephan R over
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Patent number: 5561148Abstract: Novel oxazolidinone derivatives of the formula I ##STR1## in which R.sup.1 is a phenyl radical which is unsubstituted or is monosubstituted by CN, H.sub.2 N--CH.sub.2 --, A.sub.2 N--CH.sub.2 --, H.sub.2 N--C(.dbd.NH)--, H.sub.2 N--C(.dbd.NH)--NH--, H.sub.2 N--C(.dbd.NH)--NH--CH.sub.2 --, HO--NH--C(.dbd.NH)-- or HO--NH--C(.dbd.NH)--NH--,X is O, S, SO, SO.sub.2, --NH-- or --NA--,B is ##STR2## or ##STR3## A is alkyl having from 1 to 6 C atoms,R.sup.2 is H, A, Li, Na, K, NH.sub.4 or benzyl,R.sup.3 is H or (CH.sub.2).sub.n --COOR.sup.2,E is, in each case independently of each other, CH or N,Q is O, S or NH,m is 1, 2 or 3, andn is 0, 1, 2 or 3,and physiologically compatible salts thereof are provided, which inhibit the binding of fibrinogen to the corresponding receptor and can be used for treating thrombosis, stroke, cardiac infarction, inflammations, arteriosclerosis, osteoporosis and also tumors.Type: GrantFiled: September 22, 1994Date of Patent: October 1, 1996Assignee: Merck Patent Gesellschaft Mit Beshrankter HaftungInventors: Joachim Gante, Horst Juraszyk, Peter Raddatz, Hanns Wurziger, Guido Melzer, Sabine Bernotat-Danielowski
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Patent number: 5559111Abstract: .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: April 4, 1995Date of Patent: September 24, 1996Assignee: Ciba-Geigy CorporationInventors: Richard G oschke, J urgen K. Maibaum, Walter Schilling, Stefan Stutz, Pascal Rigollier, Yasuchika Yamaguchi, Nissim C. Cohen, Peter Herold
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Patent number: 5541080Abstract: A process is provided for preparing an L-.alpha.-amino acid from a 5(4H)-oxazolone precursor. The precursor is subjected to a two-step process sequence in which the precursor is first contacted with a methanolytically active lipase in the presence of methanol in a non-polar solvent to enantioselectively solvolyze the precursor and produce an intermediate optically active methyl ester of the desired .alpha.-amino acid. This ester is then contacted with a protease in the presence of water to enantioselectively cleave the ester and accomplish an enzymatic kinetic resolution to prepare the product L-.alpha.-amino acid in high optical purity.Type: GrantFiled: May 28, 1993Date of Patent: July 30, 1996Assignee: Wisconsin Alumni Research Fdn.Inventor: Charles J. Sih
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Patent number: 5523403Abstract: A novel class of phenyloxazolidinone antibacterial agents which have, as their salient structural feature, an appended substituted tropone moiety, are described. Intermediates and processes for the preparation of these antibiotics are also disclosed. These compounds are useful antibacterial agents to eradicate or control susceptible organisms. ##STR1## wherein R.sup.4 is oxygen substituted heptatrienyl and R.sup.1, R.sup.2, and R.sup.3 are as defined herein.Type: GrantFiled: May 22, 1995Date of Patent: June 4, 1996Assignee: The Upjohn CompanyInventor: Michael R. Barbachyn
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Patent number: 5512688Abstract: Sulphonic acid esters of formula ##STR1## wherein R1 is lower-alkyl or phenyl, useful as intermediates in the production of .beta.-aminoalcohols.Type: GrantFiled: March 9, 1995Date of Patent: April 30, 1996Assignee: Hoffmann-La Roche Inc.Inventor: Hans Hilpert
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Patent number: 5455353Abstract: A process for the production of a .beta.-aminoalcohol 2-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS) -isoquinoline-3(S)-carboxamide of the formula ##STR1## via the oxazolidinone corresponding to the aminoalcohol 10, as well as intermediates occurring in this process.Type: GrantFiled: March 9, 1994Date of Patent: October 3, 1995Assignee: Hoffmann-La Roche Inc.Inventor: Hans Hilpert
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Patent number: 5424325Abstract: Aminoketone derivatives according to the present invention strongly inhibit thiol protease such as calpain, papain, cathepsin B, cathepsin H, cathepsin L or the like and have excellent properties concerning absorbance on oral administration, tissue distribution and cell membrane permeability. The aminoketone derivatives cart thus be used as therapeutic agents for treating muscular dystrophy, cataract, cardiac infarction, stroke, Alzheimer's disease, amyotrophy, osteoporosis and hypercalcemia and so on. It may also be used as therapeutic agents for preventing metastasis of cancer. In addition, the present derivatives are also applicable as intermediates for the preparation of ketone derivatives, which have inhibitory activity against thiol protease.Type: GrantFiled: December 22, 1993Date of Patent: June 13, 1995Assignee: Mitsubishi Kasei CorporationInventors: Ryoichi Ando, Naoko Ando, Hirokazu Masuda, Toshiro Sasaki, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
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Patent number: 5420132Abstract: A compound of formula (I): ##STR1## wherein: X represents O, S or H.sub.2,R and R' each represents hydrogen or together form a bond,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the description.useful in the treatment or prevention of disorders involving oxidative processes.Type: GrantFiled: May 6, 1994Date of Patent: May 30, 1995Assignee: Adir et CompagnieInventors: Gerald Guillaumet, Gerard Coudert, Valerie Thiery, Gerard Adam, Jean-Guy Bizot-Espiard, Bruno Pfeiffer, Pierre Renard
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Patent number: 5412100Abstract: Fungicidal substituted acrylic esters of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or alkenyl, or represents in each case optionally substituted aralkyl, aralkenyl, aryl or heteroaryl,R.sup.2 represents halogen, cyano, nitro, formyl, halogenoalkyl, alkoxyalkyl or alkylthioalkyl, or represents hydroximinoalkyl, alkoximinoalkyl, N-alkyliminoalkyl, N-aryliminoalkyl or N,N-dialkylhydrazonoalkyl, or represents alkoxy, alkylthio, halogenoalkoxy or halogenoalkylthio, or represents aryloxy or arylthio, or represents alkanoyl, alkoxycarbonyl, N,N-dialkylcarbamoyl or heterocyclylcarbonyl,R.sup.3 represents alkyl, or represents optionally substituted aralkyl,R.sup.4 represents dialkylamino or represents a radical --Z--R.sup.5,X represents oxygen or sulphur andY represents oxygen or sulphur or represents a radical ##STR2## where R.sup.5 represents alkyl or represents optionally substituted aralkyl,R.sup.Type: GrantFiled: July 1, 1993Date of Patent: May 2, 1995Assignee: Bayer AktiengesellschaftInventors: Alexander Klausener, Gerd Kleefeld, Wilhelm Brandes, Stefan Dutzmann, Gerd Hanssler
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Patent number: 5376670Abstract: The present invention is novel compounds which are 3,5-di-tertiary-butyl-4-hydroxyphenyl substituted 1,2,4- and 1,3,4-thiadazoles and oxadiazoles, and 1,2,4-triazoles, and pharmaceutically acceptable additions and base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and the like.Type: GrantFiled: July 13, 1993Date of Patent: December 27, 1994Assignee: Warner-Lambert CompanyInventors: David T. Connor, Daniel L. Flynn, Catherine R. Kostlan, Michael D. Mullican, Gary P. Shrum, Paul C. Unangst, Michael W. Wilson
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Patent number: 5348969Abstract: A novel series of oxazole derivatives having enhanced water solubility bioavailability and metabolic stability is disclosed in the Formula I ##STR1## Y is CH.sub.3, Ph, or OH, provided that when Y is OH, the compound exists in the keto-enol tautaumerism form ##STR2## R.sup.1 is Ph or Th; R.sup.2 is H or CH.sub.2 R.sup.3 ;R.sup.3 is H, OCH.sub.3, C.sub.1 -C.sub.5 lower alkyl, or CO.sub.2 R.sup.4 ;R.sup.4 is H or C.sub.1 -C.sub.5 lower alkyl;R.sup.5 is H or CH.sub.3 ;R.sup.6 is OHCHN or H.sub.2 N; andR.sup.7 is H or OH;or pharmaceutically acceptable salt thereof.The compounds are useful as inhibitors of ADP-induced blood platelet aggregation in human platelet-rich plasma.Type: GrantFiled: April 3, 1992Date of Patent: September 20, 1994Assignee: Bristol-Myers Squibb CompanyInventors: Jeffrey L. Romine, Nicholas A. Meanwell
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Patent number: 5332754Abstract: A naphthyloxazolidone derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen atom, hydroxy group, nitro group, amino group, sulfo group, aminosulfonyl group, a lower alkenyloxy group, a lower alkynyloxy group, a mono or di(lower alkyl)aminocarbonyloxy group, a lower alkanoyloxy group or a lower alkoxy group which may have a substituent selected from an aryl group, a cycloalkyl group, an oxygen-containing heteromonocyclic group, hydroxy group, a lower alkoxy group, cyano group, a di(lower alkyl)amino group, aminocarbonyl group, a lower alkoxycarbonyl group, a lower alkanoyloxy group, a lower alkylthio group, a lower alkylsulfinyl group and a lower alkylsulfonyl group; R.sup.2 is hydroxy group, a lower alkoxy group, a lower alkylsulfonyloxy group, triazo group or an amino group which may have a substituent selected from a lower alkyl group and a lower alkanoyl group, and a pharmaceutically acceptable salt thereof are disclosed.Type: GrantFiled: October 15, 1992Date of Patent: July 26, 1994Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Hideo Nakai, Koichiro Yamada, Sumihiro Nomura, Mamoru Matsumoto, Hiroshi Iwata
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Patent number: 5332741Abstract: The invention relates to compounds of the formula I: ##STR1## in which R.sub.1 is as defined in the description, their optical isomers and their addition salts with a pharmaceutically-acceptable acid or base, andmedicinal products which are useful for treating Central Nervous System disorders.Type: GrantFiled: May 17, 1993Date of Patent: July 26, 1994Assignee: Adir et CompagnieInventors: Gerald Guillaumet, Gerard Coudert, Tchao Podona, Beatrice Guardiola-Lemaitre, Pierre Renard, Gerard Adam, Daniel Henri-Caignard
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Patent number: 5324723Abstract: 1,3-Oxazole and 1,3-thiazole compounds of formula I, and their pharmaceutically acceptable salts and prodrugs: ##STR1## wherein X represents oxygen or sulphur;R.sup.1 represents a non-aromatic azacyclic or azabicyclic ring system.Type: GrantFiled: July 1, 1993Date of Patent: June 28, 1994Assignee: Merck Sharpe & Dohme Ltd.Inventors: Raymond Baker, John Saunders, Roger J. Snow, Graham A. Showell
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Patent number: 5276037Abstract: The invention concerns an aryl derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X.sup.1 is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X.sup.1 is a group of the formula--X.sup.4 --CR.sub.2 -- or --CR.sub.2 --X.sup.4 --whereinX.sup.4 is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl;each of Ar.sup.2 and Ar.sup.3 is optionally substituted phenylene;X.sup.2 is oxy, thio, sulphinyl or sulphonyl;R.sup.1 is (1-4C)alkyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X.sup.3 --A.sup.2 -- which together with the carbon atom to which A.sup.1 and A.sup.2 are attached define a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X.sup.Type: GrantFiled: April 14, 1993Date of Patent: January 4, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
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Patent number: 5272163Abstract: Amides having formula I: ##STR1## wherein E, X, R.sup.2 and R.sup.3 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolysable esters thereof, which are useful in the treatment of urinary incontinence. Further provided are processes for preparing the amides and pharmaceutical compositions containing them.Type: GrantFiled: July 23, 1992Date of Patent: December 21, 1993Assignees: Imperial Chemical Industries PLC, Imperial Chemical HouseInventors: Keith Russell, Cyrus J. Ohnmacht, Keith H. Gibson
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Patent number: 5268484Abstract: 5-alkoxymethyl or alkenyloxymethyl-2-oxazolidines, particularly those having a long chain alkyl or alkenyl moiety are useful as a internal mold release in the polyurea reaction injection molding technology.Type: GrantFiled: September 4, 1992Date of Patent: December 7, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Toshiyuki Ishii, Mitsuo Yamada
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Patent number: 5254577Abstract: Novel aminomethyloxooxazolidinyl arylbenzene derivatives, wherein the aryl includes the phenyl, substituted phenyl, pyridyl, and substituted pyridyl groups, such as (l)-N-{3-[4-(4'-pyridyl)phenyl]-2-oxooxazolidin-5-ylmethyl}acetamide, possess useful antibacterial activity.Type: GrantFiled: August 14, 1992Date of Patent: October 19, 1993Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Randall K. Carlson, Chung-Ho Park, Walter A. Gregory
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Patent number: 5243056Abstract: Intermediates of Formula ##STR1## where R is a methylthio, methylsulfoxy, methylsulfonyl or a nitro group; andX1 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl, phenyl or phenylalkyl(1-6 C), where the phenyl ring may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX1 together with X2 is an oxygen atom or an alkylene having from two to five Carbon atoms; orX1 together with X2 and R4 is a chain of formula ##STR2## where p is 3 or 4 and q is 1 or 2; and X2 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl or phenyl which may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX2 together with X1 has the above mentioned meanings; orX2 together with R4 is --(CH.sub.2).sub.m --CH.dbd.CH--; --(CH.sub.2).sub.m --CH.sub.2 --CH.sub.Type: GrantFiled: February 25, 1992Date of Patent: September 7, 1993Assignee: Zambon S.p.A.Inventors: Giancarlo Jommi, Dario Chiarino
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Patent number: 5235063Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is an oxygen atom, a methylene group or a --CH.dbd.CH-- group;n is 1 or 2 when X is an oxygen atom or a methylene group and is 0 or 1 when X is a --CH.dbd.CH-- group;R.sub.3 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl, benzyl, CHF.sub.2, CF.sub.3 or CF.sub.3 CF.sub.2 group;each of R.sub.2 and R'.sub.2 independently is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl group;R'.sub.2 and R.sub.3 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain; andeach of R.sub.4 and R'.sub.4 independently is a C.sub.1 -C.sub.4 alkyl group or R.sub.4 and R'.sub.4 form together either a --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.3 -- chain, a --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.3 -- chain substituted by one or two C.sub.1 -C.sub.4 alkyl groups, or a --(CH.sub.2).sub.2 -- chain substituted by one or two --CH.sub.2 --NH.sub.Type: GrantFiled: July 18, 1991Date of Patent: August 10, 1993Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
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Patent number: 5196543Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is either an oxygen atom, in which case R.sub.2 =H or halogen, or a methylene group or a --CH.dbd.CH-- group, in which case R.sub.2 =H;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group; each of R.sub.3 and R.sub.4 is independently H, C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.5 is H or C.sub.1 -C.sub.4 alkyl;R.sub.6 is C.sub.1 -C.sub.4 alkyl, CHF.sub.2, CF.sub.3, CF.sub.3 CF.sub.2, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.4 and R.sub.6 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --chain;R.sub.5 and R.sub.6 may further form together a --(CH.sub.2).sub.4 --or --(CH.sub.2).sub.5 --chain; andR.sub.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 acyl or benzyl,useful as drugs, prepared by cyclizing N ethoxy carbonyl anilines with substituted 1, 3 dioxolane-2-ones.Type: GrantFiled: July 19, 1991Date of Patent: March 23, 1993Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
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Patent number: 5192782Abstract: This invention relates to compounds of Formula I and the stereoisomers and pharmaceutically acceptable salts thereof ##STR1## wherein R is alkyl, alkenyl, alkynyl, or (CH.sub.2).sub.m R.sup.3 whereR.sup.3 is cycloalkyl and m is 1 or 2;R.sup.1 is alkyl;R.sup.2 is hydrogen or alkyl;R.sup.4 is alkyl;n is an integer from 1 to 5;p is an integer from 0 to 6;Y is oxygen; andZ is hydrogen, alkyl, alkoxy, NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen or alkyl, or SR.sup.6 wherein R.sup.6 is hydrogen, benzyl or alkyl.The compounds of Formula I are leukotriene B.sub.4 antagonists and are useful as anti-inflammatory agents and in the treatment of leukotriene B.sub.4 mediated conditions.Type: GrantFiled: September 13, 1991Date of Patent: March 9, 1993Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Thomas D. Penning, James P. Snyder
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Patent number: 5187271Abstract: A class of N-substituted (.alpha.-imidazolyl-toluyl)pyrrole compounds described for use in treatment of circulatory disorders. Compounds of particular interest are angiotensin II antagonists of the formula ##STR1## wherein m is one; wherein each of R.sup.0 and R.sup.1 is independently selected from hydrido, alkyl, hydroxyalkyl, formyl, halo, haloalkyl, cycloalkylcarbonyl, alkoxy, aroyl, aryloxy, aralkoxy, alkylcarbonyl, alkoxycarbonyl, cyano, nitro, carboxyl, alkylcarbonyloxy, alkylcarbonyloxyalkyl, alkoxycarbonylalkyl, aralkoxycarbonylalkyl, alkylsulfonyl, aralkylsulfonyl, arylsulfonyl; wherein R.sup.2 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclohexyl, cyclohexylmethyl, propylthio, butylthio, and hydroxyalkyl; wherein each of R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.Type: GrantFiled: February 28, 1991Date of Patent: February 16, 1993Assignee: G. D. Searle & Co.Inventors: Philippe R. Bovy, Joe T. Collins, Robert E. Manning
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Patent number: 5182403Abstract: The present invention relates to 3 indazol substituted 5 Beta amidomethyloxazolidin-2ones, useful as antibacterial agents and to intermediates for their production.Type: GrantFiled: April 23, 1992Date of Patent: January 26, 1993Assignee: The Upjohn CompanyInventor: Steven J. Brickner
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Patent number: 5182296Abstract: A naphthyloxazolidone derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen atom, hydroxy group, nitro group, amino group, sulfo group, aminosulfoyul group, a lower alkenyloxy group, a lower alkynyloxy group, a mono or di(lower alkyl)aminocarbonyloxy group, a lower alkanoyloxy group or a lower alkoxy group which may have a substituent selected from an aryl group, a cycloalkyl group, an oxygen-containing heteromonocyclic group, hydroxy group, a lower alkoxy group, cyano group, a di(lower alkyl)amino group, aminocarbonyl group, a lower alkoxycarbonyl group, a lower alkanoyloxy group, a lower alkylthio group, a lower alkylsulfinyl group and a lower alkylsulfonyl group; R.sup.2 is hydroxy group, a lower alkoxy group, a lower alkylsulfonyloxy group, triazo group or an amino group which may have a substituent selected from a lower alkyl group and a lower alkanoyl group, and a pharmaceuticaly acceptable salt thereof are disclosed.Type: GrantFiled: October 18, 1990Date of Patent: January 26, 1993Assignee: Tanabe Seiyaky Co., Ltd.Inventors: Hideo Nakai, Koichiro Yamada, Shumihiro Nomura, Mamoru Matsumoto, Hiroshi Iwata
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Patent number: 5171747Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is an oxygen atom, a methylene group or a --CH.dbd.CH-- group;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group;D is an oxygen atom or a NOR group, wherein R.dbd.H or C.sub.1 -C.sub.4 alkyl;R.sub.3 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group;each of R.sub.2 and R'.sub.2 independently is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group; andR'.sub.2 and R.sub.3 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain,useful as drugs.Type: GrantFiled: October 16, 1990Date of Patent: December 15, 1992Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
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Patent number: 5164510Abstract: The present invention relates to 5'-indolinyloxazolidin-2-ones (XI) ##STR1## 3-(fused-ring) substituted)phenyl-5.beta.-amidomethyloxazolidin-2-ones (XXI) ##STR2## and 3-(nitrogen substituted)phenyl-5.beta.-amidomethyloxazolidin-2-ones (LV) which are useful as antibacterial agents and the intermediates (VI), (VII) and (VIII) useful for their production.Type: GrantFiled: February 20, 1991Date of Patent: November 17, 1992Assignee: The Upjohn CompanyInventor: Steven J. Brickner
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Patent number: 5151439Abstract: The present invention discloses substituted 1,3-benzodioxoles which possess anti-diabetic and/or anti-hyperglycemic and/or anti-obesity properties in humans and other animals.Type: GrantFiled: August 1, 1991Date of Patent: September 29, 1992Assignee: American Cyanamid CompanyInventors: Jonathan D. Bloom, Thomas H. Claus, Vern G. DeVries, Jo A. Dolan, Minu D. Dutia
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Patent number: 5110986Abstract: This application relates to a process for preparing a N-t-alkyl-1,2-diacylhydrazine by reacting a 1,3,4-oxadiazole with a tertiary alkyl cation precursor in the presence of a strong acid catalyst. Preferably, the 1,3,4-oxadiazole is a 2,5-disubstituted-1,3,4-oxadiazole and more preferably a 2,5-diaryl-1,3,4-oxadiazole. The strong acid catalyst is preferably a sulfur containing acid and more preferably sulfuric acid.Type: GrantFiled: April 26, 1988Date of Patent: May 5, 1992Assignee: Rohm and Haas CompanyInventor: Martha J. Kelly
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Patent number: 5105009Abstract: Intermediates of Formula ##STR1## where R is a methylthio, methylsulfoxy, methylsulfonyl or a nitro group; andX1 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl, phenyl or phenylalkyl(1-6C), where the phenyl ring may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX1 together with X2 is an oxygen atom or an alkylene having from two to five Carbon atoms; orX1 together with X2 and R4 is a chain of formula ##STR2## where p is 3 or 4 and q is 1 or 2; and X2 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl or phenyl which may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX2 together with R4 is ##STR3## where n is 1 or 2; m is 0 or 1; X is hydrogen, halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; andX3 is hydrogen or --CO--R4 where R4 is hydrogen, 1-6 alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl, phenylalkyl(1-6C) or phenyl where the phenyl ring may be substituted by one or two halogen, 1-3 alkyl, 1-3 alkoxy or nitro; andX4 is --OH, fluorine,Type: GrantFiled: February 29, 1988Date of Patent: April 14, 1992Assignee: Zambon S.p.A.Inventors: Giancarlo Jommi, Dario Chiarino
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Patent number: 5103007Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.Type: GrantFiled: October 27, 1989Date of Patent: April 7, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
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Patent number: 5081245Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.Type: GrantFiled: August 18, 1989Date of Patent: January 14, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
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Patent number: 5066662Abstract: Oxazolidin-2-ones and 1,2,4-oxadiazolin-5-ones substituted in the 4-position of the oxazolidin-2-one ring and the 3-position of the 1,2,4-oxadiazolin-5-one ring with a 5- or 6-member heteroaromatic, a bicyclic heteroaromatic group or a 5- or 6-member heterocyclic group either directly or via a one or two carbon bridge and derivatives thereof are described, as well as methods for the preparation and pharmaceutical compositions of same, which are useful as centrally acting muscarinic agents and are useful as analgesic agents for the treatment of pain, as sleep aids and as agents for treating the symptoms of senile dementia, Alzheimer's disease, Huntington's chorea, tardive dyskinesia, hyperkinesia, mania, or similar conditions of cerebral insufficiency characterized by decreased cerebral acetycholine production or release.Type: GrantFiled: May 21, 1990Date of Patent: November 19, 1991Assignee: Warner-Lambert CompanyInventors: Sheila H. Hobbs, Stephen J. Johnson
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Patent number: 5043454Abstract: 1-Aryl- and 1-hetarylimidazolecarboxylic esters of the general formulae Ia and Ib ##STR1## where R.sup.1 is halogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl;R.sup.2 is substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl; C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.6 -cycloalkyl;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 -alkyl;R.sup.4 is substituted or unsubstituted phenyl or 5- or 6-membered heteroaromatic,processes for their manufacture, and agents containing them.Type: GrantFiled: January 9, 1990Date of Patent: August 27, 1991Assignee: BASF AktiengesellschaftInventors: Ulrich Wriede, Gerhard Hamprecht, Hermann Koehler, Bruno Wuerzer
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Patent number: 5043443Abstract: Novel aminomethyloxooxazolidinyl arylbenzene derivatives, wherein the aryl includes the phenyl, substituted phenyl, pyridyl, and substituted pyridyl groups, such as (l)-N-{3-[4- (4'-pyridyl)phenyl]-2-oxooxazolidin-5-ylmethyl}acetamide, possess useful antibacterial activity.Type: GrantFiled: July 24, 1990Date of Patent: August 27, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Randall K. Carlson, Chung-Ho Park, Walter A. Gregory
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Aminomethyl oxooxazolidinyl oxa or thia cycloalkylbenzene derivatives useful as antibacterial agents
Patent number: 5039690Abstract: Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives, such as l-N-[3-(2,3-dihydro-oxa or thio-lH-inden-5-yl)-2-oxooxazolidin-5-ylmethyl]acetamide, possess useful antibacterial activity.Type: GrantFiled: March 15, 1990Date of Patent: August 13, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Chia-Lin J. Wang, Mark A. Wuonola -
Patent number: 5036091Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is either an oxygen atom, in which case R.sub.2 =H or halogen, or a methylene group or a --CH.dbd.CH-- group, in which case R.sub.2 =H;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group;each of R.sub.3 and R.sub.4 is independently H, C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.5 is H or C.sub.1 -C.sub.4 alkyl;R.sub.6 is C.sub.1 -C.sub.4 alkyl, CHF.sub.2, CF.sub.3, CF.sub.3 CH.sub.2, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.4 and R.sub.6 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain;R.sub.5 and R.sub.6 may further form together a --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- chain; andR.sub.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 acyl or benzyl,useful as drugs.Type: GrantFiled: October 15, 1990Date of Patent: July 30, 1991Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
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Patent number: 5036090Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is an oxygen atom, a methylene group or a --CH.dbd.CH-- group;n is 1 or 2 when X is an oxygen atom or a methylene group and is 0 or 1 when X is a --CH.dbd.CH-- group;R.sub.3 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl, benzyl, CHF.sub.2, CF.sub.3 or CF.sub.3 CF.sub.2 group;each of R.sub.2 and R'.sub.2 independently is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl group;R'.sub.2 and R.sub.3 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain; andeach of R.sub.4 and R'.sub.4 independently is a C.sub.1 -C.sub.4 alkyl group or R.sub.4 and R'.sub.4 form together either a --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.3 -- chain, a --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.3 -- chain substituted by one or two C.sub.1 -C.sub.4 alkyl groups, or a --(CH.sub.2).sub.2 -- chain substituted by one or two --CH.sub.2 --NH.sub.Type: GrantFiled: October 15, 1990Date of Patent: July 30, 1991Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
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Patent number: 5036093Abstract: Aminomethyl oxooxazolidinyl azacycloalkylbenzene derivatives, such as l-N-[3-(2,3-dihydro-3-aza-1H-inden-5-yl)-2-oxooxazolidin-5-ylmethyl]acetam ide, possess useful antibacterial activity.Type: GrantFiled: March 15, 1990Date of Patent: July 30, 1991Assignee: Du Pont Merck PharmaceuticalInventors: Chia-Lin J. Wang, Mark A. Wuonola
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Patent number: 5036092Abstract: Aminomethyl oxooxazolidinyl aza cycloalkylbenzene derivatives, such as l-N-[3-(2,3-dihydro-3-aza-1H-inden-5-yl)-2-oxooxazolidin-5-ylmethyl]acetam ide, possess useful antibacterial activity.Type: GrantFiled: March 15, 1990Date of Patent: July 30, 1991Assignee: Du Pont Merck PharmaceuticalInventors: Chia-Lin J. Wang, Mark A. Wuonola