Oxadiazole Ring (including Hydrogenated) Patents (Class 544/138)
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Patent number: 6395897Abstract: Disclosed are cathepsin S reversible inhibitory compounds of the formulas (I),(Ia) and (II),(IIa) as defined herein. The compounds are useful for treating autoimmune diseases. Also disclosed are processes for making such novel compounds.Type: GrantFiled: November 5, 1999Date of Patent: May 28, 2002Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.Inventors: Charles L. Cywin, Michel J. Emmanuel, Leah L. Frye, Denice M. Spero, David S. Thomson, Yancey D. Ward
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Publication number: 20010051621Abstract: The invention is a novel crystal form (Form II) of a known compound, linezolid 1Type: ApplicationFiled: January 29, 2001Publication date: December 13, 2001Inventor: Michael S. Bergren
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Patent number: 6277872Abstract: The invention relates to oxadiazole derivatives of general formula (I) wherein X, Y, Z and R1 are defined as described in the specification and claims, processes for preparing them and their use as pharmaceutical compositions.Type: GrantFiled: July 26, 1999Date of Patent: August 21, 2001Assignee: Boehringer Ingelheim KGInventors: Michael Brenner, Roland Maier, Marion Wienrich, Thomas Weiser, Rainer Palluk, Wolf-Dietrich Bechtel, Angelo Sagrada, Helmut Ensinger, Uwe Pschorn, Raffaele Cesana
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Patent number: 6255304Abstract: The present invention provides compounds of Formula 1 or pharmaceutical acceptable salts thereof wherein A, G and R, are as defined in the claims which are antibacterial agents.Type: GrantFiled: November 27, 1998Date of Patent: July 3, 2001Assignee: Pharmacia & Upjohn CompanyInventors: Jackson B. Hester, Jr., Eldon George Nidy, Salvatore Charles Perricone, Toni-Jo Poel
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Patent number: 6100259Abstract: Novel pyrazole derivatives are provided which are cannabinoid receptor modulators.Type: GrantFiled: October 15, 1999Date of Patent: August 8, 2000Assignee: SmithKline Beecham CorporationInventors: Jia-Ning Xiang, John Duncan Elliott, Steven Todd Atkinson, Siegfried Benjamin Christensen, IV
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Patent number: 6087359Abstract: A thioaryl sulfonamide hydroxamic acid compound that inter alia inhibits matrix metalloprotease activity is disclosed as are a treatment process that comprises administering a contemplated thioaryl sulfonamide hydroxamic acid compound in a MMP enzyme-inhibiting effective amount to a host having a condition associated with pathological matrix metalloprotease activity.Type: GrantFiled: September 10, 1999Date of Patent: July 11, 2000Inventors: Daniel P. Getman, Daniel P. Becker, Thomas E. Barta, Clara I. Villamil, Susan L. Hockerman, Louis J. Bedell, Hui Li, John N. Freskos, Robert M. Heintz, Joseph J. McDonald, Gary A. DeCrescenzo
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Patent number: 6051572Abstract: A class of azetidine, pyrrolidine and piperidine derivatives, substituted by inter alia a phenylmorpholinyl, phenylpiperidinyl or benzimidazolone moiety, are selective agonists of 5-HT.sub.1 -like receptors, being potent agonists of the human 5-HT.sub.1D.alpha. receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT.sub.1D.alpha. receptor subtype relative to the 5-HT.sub.1D.beta. subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT.sub.1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT.sub.1D receptor agonists.Type: GrantFiled: April 28, 1998Date of Patent: April 18, 2000Assignee: Merck Sharp & Dohme Ltd.Inventor: Jose Luis Castro Pineiro
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Patent number: 5965579Abstract: The invention relates to compounds of the formula: ##STR1## Compounds of the above formula have a great affinity for the neurotensin receptors.Type: GrantFiled: November 21, 1997Date of Patent: October 12, 1999Assignee: SanofiInventors: Bernard Labeeuw, Danielle Gully, Francis Jeanjean, Jean-Charles Molimard, Robert Boigegrain
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Patent number: 5914351Abstract: Compounds of the formula ##STR1## wherein Q is a hydrazone derivative;R.sup.1 is hydrogen, halogen, alkyl or alkoxy;R.sup.2 is hydrogen, halogen, alkyl, alkoxy, alkenoxy, alkynyloxy, halomethyl, trifluoromethoxy, alkylthio, nitro or cyano; andR.sup.6 is a substituted carboxamide, carbothioamide, phosphonosoamide, or phosphonothioamide,useful as anti-HIV agents.Type: GrantFiled: December 12, 1997Date of Patent: June 22, 1999Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Co./CIE.Inventors: Walter Gerhard Brouwer, Ewa Maria Osika
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Patent number: 5877316Abstract: The present invention relates to compounds of formula (I), wherein R.sup.1 and R.sup.4 represent hydrogen, halogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkylC.sub.1-4 alkyl, C.sub.1-6 alkoxy, C.sub.1-4 alkyl substituted by a hydroxy or C.sub.1-4 alkoxy group, OCF.sub.3, hydroxy, trifluoromethyl, trimethylsilyl, nitro, CN, SR.sup.a, SOR.sup.a, SO.sub.2 R.sup.a, COR.sup.a, CO.sub.2 R.sup.a or CONR.sup.a R.sup.b, where R.sup.a and R.sup.b are each independently hydrogen or C.sub.1-4 alkyl; R.sup.2, R.sup.3 and R.sup.5 represent hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy substituted by a C.sub.1-4 alkoxy group, or trifluoromethyl; R.sup.6 represents C.sub.1-6 alkyl, optionally substituted by oxo, substituted by a 5-membered heteroaromatic ring selected from oxazole, thiazole, isoxazole, isothiazole, oxadiazole and thiadiazole, wherein each heteroaromatic ring is substituted at the available carbon atom by a group of the formula: ZNR.sup.7 R.sup.8.Type: GrantFiled: September 16, 1997Date of Patent: March 2, 1999Assignee: Merck Sharp & Dohme Ltd.Inventors: Karen Elizabeth Haworth, Simon Neil Owen, Eileen Mary Seward
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Patent number: 5854179Abstract: Sulfur-substituted phenylsulfonylureas; processes for their preparation and their use as herbicides and plant growth regulatorsCompounds of the formula (I) and salts thereof ##STR1## in which R*, R.sup.1, R.sup.2, R.sup.3, X, Y, Z, W, n and m are defined as in claim 1, and specifically R* is a formyl equivalent of the formula CHO, --CH.dbd.NR or CH(X.sup.1 R')(X.sup.2 R"), are suitable as herbicides and plant growth regulators. They are prepared analogously to known methods, in some cases using novel intermediate products of the formula (XVII) ##STR2## in which U*.dbd.NH.sub.2, Cl or (substituted) amino.Type: GrantFiled: November 3, 1995Date of Patent: December 29, 1998Assignee: Hoechst Schering AgrEvo GmbHInventors: Gerhard Schnabel, Lothar Willms, Klaus Bauer, Hermann Bieringer, Christopher Rosinger
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Patent number: 5852011Abstract: Disclosed are compounds represented by the following chemical formula (I) and pharmacologically acceptable salts thereof which are novel compounds useful as anticancer agents, antiviral agents or antimicrobial agents.Type: GrantFiled: January 19, 1996Date of Patent: December 22, 1998Assignee: Mitsui Chemicals, Inc.Inventors: Akio Matsunaga, Yuki Nakajima, Hiroshi Kohno, Hironori Komatsu, Hajime Edatsugi, Daiji Iwata, Kimiko Takezawa
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Patent number: 5840721Abstract: The present invention relates to polysubsituted imidazole having formula 1 ##STR1## These compounds are useful for restoring the sensitivity of multidrug resistant cells to cancer chemotherapeutic agents.Type: GrantFiled: October 16, 1997Date of Patent: November 24, 1998Assignee: Ontogen CorporationInventors: Adnan M. M. Mjalli, Chengzhi Zhang
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Patent number: 5837702Abstract: Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein X is alkyl, Y is a single bond, --CH.sub.2 --, --C(O)--, --O--, --S-- or --N(R.sup.8)-- where R.sup.8 is hydrogen, alkyl, haloalkyl, aryl, arylalkyl, cycloalkyl or (cycloalkyl)alkyl, and R.sup.1 to R.sup.7 are as defined herein. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.Type: GrantFiled: August 30, 1994Date of Patent: November 17, 1998Assignee: Bristol-Myers Squibb Co.Inventors: George C. Rovnyak, Karnail S. Atwal, Dinos P. Santafianos, Charles Z. Ding
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Patent number: 5801170Abstract: A compound of formula (I) or a salt thereof: ##STR1## wherein P is a 5 to 7 membered heterocyclic ring selected from the group consisting of thienyl, furyl, pyrrolyl, triazolyl, diazolyl, tetrazolyl, imidazolyl, oxadiazolyl, isothiazolyl, isoxazolyl, thiadiazolyl, pyridyl, pyrimdyl and pyrazinyl;R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen, halogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkenyl, C.sub.1-6 alkoxy, hydroxyC.sub.1-6 alkyl, C.sub.1-6 alkylOC.sub.1-6 alkyl, alkanoyl, optionally substituted phenyl, alkanoyloxy, hydroxy, nitro, trifluoromethyl, cyano, CO.sub.2 R.sup.9,CONR.sup.10 R.sup.11 where R.sup.9, R.sup.10 and R.sup.11 are independently hydrogen or C.sub.1-6 alkyl;R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1-6 alkyl;R.sup.6 is hydrogen, halogen, hydroxy, C.sub.1-6 alkyl or C.sub.1-6 alkoxyR.sup.7 and R.sup.8 are independently hydrogen, C.sub.Type: GrantFiled: June 7, 1996Date of Patent: September 1, 1998Assignee: SmithKline Beecham plcInventors: Laramie Mary Gaster, Francis David King, Paul Adrian Wyman
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Patent number: 5770598Abstract: The present invention relates to heterocyclic compounds which have been found to have anti-tumour activity. More specifically, the invention concerns Pyrrolo ?3,2-b! carbazoles, 1H-Benzofuro ?3,2-.function.! indoles and 1H-?1! Benzothieno ?2,3-.function.! indoles, methods for their preparation, pharmaceutical formulations containing them and their use as anti-tumour agents.Type: GrantFiled: April 10, 1997Date of Patent: June 23, 1998Assignee: University College Cardiff Consultants LimitedInventors: David D. Miller, Paul Barraclough, Sadie Vile, Ann L. Walker, Patrick V. R. Shannon, Laddawan Chunchatprasert, Pierre P. M. Debont, Alan T. Hudson
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Patent number: 5665746Abstract: The present invention relates to a compound of the formula ##STR1## wherein X.sup.1, R.sup.1, R.sup.2, OP, R.sup.3, R.sup.4, R.sup.5, R.sup.6, and R.sup.0 are as described herein, and their pharmaceutically acceptable salts thereof carrying an acidic andr basic substituent.The compound of formula I as well as their pharmaceutically acceptable salts inhibit DNA gyrase activity in bacteria and possess antibiotic, especially antibacterial activity against microorganisms and can be used in the control or prevention of infectious diseases.Type: GrantFiled: October 11, 1995Date of Patent: September 9, 1997Assignee: Hoffmann-La Roche Inc.Inventors: Jurgen Geiwiz, Erwin Gotschi, Paul Hebeisen, Helmut Link, Thomas Lubbers
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Patent number: 5589473Abstract: The present invention relates to a compound of the formula ##STR1## wherein X.sup.1, R.sup.1, R.sup.2, OP, R.sup.3, R.sup.4, R.sup.5, R.sup.6, and R.sup.0 are as described herein, and their pharmaceutically acceptable salts thereof carrying an acidic and/or basic substituent.The compound of formula I as well as their pharmaceutically acceptable salts inhibit DNA gyrase activity in bacteria and possess antibiotic, especially antibacterial activity against microorganisms and can be used in the control or prevention of infectious diseases.Type: GrantFiled: March 20, 1995Date of Patent: December 31, 1996Assignee: Hoffmann-La Roche Inc.Inventors: J urgen Geiwiz, Erwin G otschi, Paul Hebeisen, Helmut Link, Thomas L ubbers
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Patent number: 5403840Abstract: The invention relates to inclusion complexes of N-ethoxycarbonyl-3-morpholino-sydnonimine or its salts formed with a cyclodextrin derivatives, preparation thereof and pharmaceutical compositions containing the same.The inclusion complex of N-ethoxycarbonyl-3-morpholino-sydnonimine or its salt formed with cyclodextrin derivative is prepared bya) reacting the N-ethoxycarbonyl-3-morpholino-sydnonimine or its salt and the cyclodextrin derivative in a solvent medium, and if desired recovering the complex from the solution by dehydration, orb) high energy milling of the N-ethoxycarbonyl-3-morpholino-sydnonimine or its salt and the cyclodextrin derivative.Type: GrantFiled: January 2, 1992Date of Patent: April 4, 1995Assignee: Chinoin Gyogyszer-Es Vegyeszeti Termekek Gyar Rt.Inventors: Maria Vikmon, Jozsef Szejtli, Jozsef Gaal, Istvan Hermecz, Agnes Horvath, Katalin Marmarosi, Gabor Horvath, Iren Munkacsi
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Patent number: 5356916Abstract: A 1,2,4-oxadiazole derivative is represented by the following general formula (I): ##STR1## wherein R.sup.1 represents a lower alkyl or cycloalkyl group, a lower alkyl group substituted with a halogen atom, a lower alkylamino group or a phenyl group; R.sup.2 represents a hydrogen atom, a lower dialkylamino group, a cyclic alkylamino group, a cyclic amino group having an oxygen or nitrogen atom in the ring, a phenyl group which may be substituted with a halogen atom, a pyridyl group, an imidazolyl group, an alkylimidazolyl group, a benzimidazolyl group or a 2-oxopyrrolidinyl group; and n is 1, 2 or 3. The derivative has excellent monoamine oxidase-inhibitory activity and is effective as a medicine for treating Parkinson's disease.Type: GrantFiled: January 31, 1992Date of Patent: October 18, 1994Assignee: Wakamoto Pharmaceutical Co., Ltd.Inventors: Hatsunori Toyofuku, Jun Matsumoto, Toshie Takahashi, Masakazu Ebie, Naomi Sasada, Mitsuzi Agata, Shohei Sawaki, Masayoshi Goto
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Patent number: 5332742Abstract: A renin inhibiting compound of the formula: ##STR1## wherein R.sub.1 is 4-piperazinyl, 1-methyl-4-piperazinyl, 1-methyl-l-oxo-4-piperazinyl, 2-oxo-4-piperazinyl, 4-morpholinyl, 4-thiomorpholinyl or 1-methyl-4-homopiperazinyl;R.sub.2 is benzyl, 2-phenylethyl, 1-naphthylmethyl or 2-naphthylmethyl;R.sub.3 is 4-thiazolyl, 2-amino-4-thiazolyl, 2-thiazolyl, 5-thiazolyl, 1-pyrazolyl, 3-pyrazolyl, 1-imidazolyl, n-propyl, isopropyl, CH.sub.3 S-- or CH.sub.3 SCH.sub.2 --;R.sub.4 is isobutyl or cyclopropyl;R.sub.5 is hydrogen or loweralkyl; andX is CH.sub.2 or NH; or a pharmaceutically acceptable salt, ester or prodrug thereof; with the proviso that when X is NH and R.sub.3 is 2-amino-4-thiazolyl, then R.sub.4 is cyclopropyl.Type: GrantFiled: November 3, 1993Date of Patent: July 26, 1994Assignee: Abbott LaboratoriesInventor: Saul H. Rosenberg
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Patent number: 5225548Abstract: Indophenol dyes of the formula ##STR1## where X is nitrogen or the radical CH,Q is a five-membered heterocyclic radical, andK is a radical of an aniline, aminonaphthalene, aminoquinoline or aminothiazole derivative, andthe radical A can be benzofused,are useful for thermal transfer processes.Type: GrantFiled: September 20, 1991Date of Patent: July 6, 1993Assignee: BASF AktiengesellschaftInventors: Volker Bach, Karl-Heinz Etzbach, Ruediger Sens
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Patent number: 5221680Abstract: Substituted 3-aminosydnonimines of the formula I ##STR1## and pharmacologically acceptable acid addition salts thereof, in which R.sup.1 denotes hydrogen or the radical --COR.sup.4,R.sup.2 denotes alkyl or phenyl alkyl having 1 to 4 C atoms in the alkyl group,R.sup.4 denotes, for example, an aryl radical, and processes and formulations for controlling or preventing cardiovascular diseases by administering an effective amount of such compounds to a host in need thereof.Type: GrantFiled: February 27, 1992Date of Patent: June 22, 1993Assignee: Cassella AktiengesellschaftInventors: Karl Schonafinger, Rudi Beyerle, Helmut Bohn
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Patent number: 5120732Abstract: Substituted 3-aminosydnone imines of the formula I ##STR1## and their pharmacologically acceptable acid addition salts, in which A denotes, for example, --CH.sub.2 --,R.sup.1 denotes hydrogen or the radical --COR.sup.5,R.sup.2, R.sup.3 denote alkyl having 1 to 4 C atoms,R.sup.5 denotes, for example, an aliphatic radical having 1 to 4 C atoms,and methods for preparing such compounds by cyclization of a compound of the formula II ##STR2## and if desired subsequent acylation. The invention also includes formulations containing effective amounts of such compounds, and methods for administering same to patients for the control and prophylaxis of cardiovascular disorders.Type: GrantFiled: August 29, 1990Date of Patent: June 9, 1992Assignee: Cassella AktiengesellschaftInventors: Karl Schonafinger, Rudi Beyerle, Helmut Bohn, Melitta Just
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Patent number: 5101034Abstract: A process for the preparation of a heteroaryloxyacetamide of the formula ##STR1## in which R is a 5 membered heterocycle which may be benzo-fused, andR.sup.1 and R.sup.2 each independently is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, halogenoalkyl, alkoxyalkyl, alkoxy, aralkyl or aryl, orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, form a heterocycle,which comprises reacting a sulphonylated heteroaromatic of the formulaR--SO.sub.2 --R'in whichR' is lower alkyl or benzyl,with an .alpha.-oxyacetamide of the formula ##STR2## in which R" is hydrogen or acyl,in the presence of an inorganic base as an acid acceptor and of solvent as a diluent at a temperature of about -50.degree. C. to +150.degree. C. The products are known herbicides.Type: GrantFiled: March 7, 1991Date of Patent: March 31, 1992Assignee: Bayer AktiengesellschaftInventors: Thomas Schmidt, Hans-Joachim Diehr
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Patent number: 5079244Abstract: Substituted 3-aminosydnone imines of the general formula I ##STR1## and their pharmacologically acceptable acid addition salts, in which A denotes an alkylene chain;X denotes one of the groups --O-- or --S--;R.sup.1 denotes e.g. hydrogen;R.sup.2 denotes e.g. an alkyl group,are prepared by cyclization of a compound of the formula II ##STR2## and, if appropriate, subsequent acylation, and have useful pharmacological properties.Type: GrantFiled: June 7, 1990Date of Patent: January 7, 1992Assignee: Cassella AktiengesellschaftInventors: Eckard Kujath, Christian Baumgartner, SchoKarl, Rudi Beyerle, Melitta Just, Helmut Bohn, Jorg Ostrowski
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Patent number: 4987132Abstract: A saturated heterocyclic carboxamide derivative of the following general formula (I) and salts thereof which have platelet activating factor (PAF) antagonizing activity.Type: GrantFiled: August 16, 1988Date of Patent: January 22, 1991Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Toshiyasu Mase, Hiromu Hara, Hitoshi Nagaoka, Takumi Takahashi, Takeshi Suzuki, Kenichi Tomioka, Toshimitsu Yamada
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Patent number: 4958043Abstract: A composition useful for incorporation into polymer compositions employed for food packaging or the like comprising a bis- or tris-methine compound having the structural formula ##STR1## wherein A is selected from the radicals ##STR2## wherein R' and R" are each selected from chlorine, bromine, fluorine, alkyl, alkoxy, aryl, aryloxy and arylthio;each n is independently 0, 1, 2;R.sub.1 is selected from a large variety of radicals such as cycloalkyl, phenyl, and straight or branched alkyl which may be substituted;R.sub.2 is alkylene or the like;R.sub.3, R.sub.4, and R.sub.5 are each selected from hydrogen and alkyl; andP and Q and P.sup.1 and Q.sup.1 are selected from cyano, carbalkoxy, carbaryloxy, carbaralkyloxy, or the like.The invention compositions are especially useful in combination with molding or fiber-grade condensation polymer; most preferably such polymer having copolymerized therein a total of from 1.Type: GrantFiled: April 18, 1988Date of Patent: September 18, 1990Assignee: Eastman Kodak CompanyInventors: Max A. Weaver, Wayne P. Pruett, Samuel D. Hilbert
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Patent number: 4952580Abstract: Polyhaloalkene compounds of the formula: ##STR1## wherein X is sulfur, oxygen, or nitrogen, Y.sup.1 and Y.sup.2 are fluorine, Z is hydrogen or the same as Y.sup.1 and Y.sup.2, and n is 1-4; provided that:(A) when X is sulfur, Z is fluorine and R is thienyl or substituted thienyl, thianaphthyl or substituted thianaphthyl, thiazolinyl or substituted thiazolinyl, oxadiazolyl or substituted oxadiazolyl, 3,4,4-trifluoro-3-butenyloxycarbonylmethyl, thiadiazolyl substituted by halogen or R.sup.2 S, wherein R.sup.2 is 3,4,4-trifluoro-3-butenyl or R.sup.2 is phenylmethyl or phenylthiomethyl each optionally substituted by halogen or nitro; or R is thiadiazolyl substituted by R.sup.3, wherein R.sup.3 is substituted aryl, arylalkyl, aryloxyalkyl, alkylthio, haloalkylthio, haloarylthio, cyanoalkylthio, arylalkylthio, aryloxyalkylthio, arylthioalkylthio, heterocycloalkylthio, alkenylthio, haloalkenylthio, halocycloalkylalkenylthio, wherein said aryl or heterocyclic groups of R.sup.Type: GrantFiled: November 9, 1988Date of Patent: August 28, 1990Assignee: FMC CorporationInventors: Anthony J. Martinez, Thomas G. Cullen
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Patent number: 4937244Abstract: Substituted 3-aminosydnonimines of the formula I ##STR1## and their pharmacologically acceptable acid addition salts wherein A denotes, for example, --CH.sub.2 --,R.sup.1 denotes hydrogen or the radical --COR.sup.7,R.sup.2, R.sup.3, R.sup.4 and R.sup.5 denote alkyl with 1 to 4 C atoms andR.sup.7 denotes, for example, an aliphatic radical and 1 to 4 C atoms, are prepared by cyclization of a compound of the formula II ##STR2## and if appropriate subsequent acylation and have useful pharmacological properties. The invention includes pharmaceutical preparations containing the present compounds, and the use thereof for treating patients having cardiovascular ailments.Type: GrantFiled: August 3, 1988Date of Patent: June 26, 1990Assignee: Cassella AktiengesellschaftInventors: Karl Schonafinger, Rudi Beyerle
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Patent number: 4888333Abstract: Substituted allylmercaptoacetylsydnonimines of the general formula I ##STR1## and their pharmacologically acceptable acid addition salts, in which R.sub.1 represents a secondary amino group of the formula ##STR2## and X denotes ##STR3## R.sub.2 denotes one of the radicals R.sub.3 OOC--, R.sub.4 SO.sub.2 -- or alkyl having1-4 C atoms,n denotes one of the values 1, 1 or 2,and R.sub.3 denotes alkyl having 1-4 C atoms,and R.sub.4 represents R.sub.3 or (R.sub.3).sub.2 N--, have valuable pharmacological properties.Type: GrantFiled: August 10, 1988Date of Patent: December 19, 1989Assignee: Cassella AktiengessellschaftInventors: Helmut Bohn, Melitta Just, Rolf-Eberhard Nitz
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Patent number: 4743595Abstract: A process for efficiently preparing 2-amino-5-nitrophenol derivatives in which benzoxazole derivatives are subjected to nucleophilic substitution reaction at the 5 position thereof to obtain corresponding benzoxazole derivatives, and the oxazole ring of the benzoxazole derivatives is then subjected to ring-opening to obtain 2-amino-5-nitrophenol derivatives. The 2-amino-5-nitrophenol derivatives are useful as industrial starting materials, reducing agents or antioxidants and intermediates for cyan-image-forming couplers.Type: GrantFiled: June 12, 1985Date of Patent: May 10, 1988Assignee: Fuji Photo Film Co., Ltd.Inventors: Isamu Itoh, Mitsunori Ono, Hidetoshi Kobayashi, Kazuyoshi Yamakawa
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Patent number: 4683228Abstract: A guanidine derivative of the formula I: ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, ring X and D are a variety of radicals defined in the specification and A is a 3-8C alkylene chain which is substituted by a hydroxy radical and into which is optionally inserted, as part of the backbone of the chain, one or two groups selected from oxygen and sulphur atoms and NH and 1-6C N-alkyl radicals; and the pharmaceutically-acceptable acid additions salts thereof. Pharmaceutical compositions and methods of manufacture are also described. The compound of the formula I is a histamine H-2 antagonist and is therefore useful in ulcer therapy.Type: GrantFiled: January 22, 1985Date of Patent: July 28, 1987Assignees: ICI Americas Inc., Imperial Chemical Industries PLCInventors: Karin M. Kirkland, Derrick M. Mant
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Patent number: 4645525Abstract: Azolyloxy-carboxylic acid amides of the formula ##STR1## wherein R is a five-membered hetero-aromatic monocyclic radical which contains an oxygen atom or a sulfur atom and 1 to 3 nitrogen atoms; orR is said monocyclic radical substituted by halogen, nitro, cyano, amino, alkylamino, dialkylamino, arylamino, alkylcarbonylamino, alkylcarbonyl, carboxyl, alkoxycarbonyl, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylaminocarbonyl substituted arylaminocarbonyl wherein the substituents are halogen, nitro or alkyl, aryl, substituted aryl wherein the substituents are halogen, nitro, cyano, alkyl, halogenoalkyl or alkoxy, aralkyl, haloaralkyl, alkoxy, halo-alkoxy, alkenoxy, alkynoxy, alkoxycarbonylalkoxy, aralkoxy or aryloxy, optionally halogen-substituted alkylthio, alkenylthio, alkynylthio, alkoxycarbonylalkylthio, aralkylthio, arylthio, alkylsulphinyl or alkylsulphonyl, optionally halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, aralkoxyalkyl, aryloxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alType: GrantFiled: August 26, 1983Date of Patent: February 24, 1987Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Wolfgang Hofer, Volker Mues, Ludwig Eue, Robert R. Schmidt
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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
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Patent number: 4618617Abstract: This disclosure describes novel 5-substituted 1,2,4-oxadiazoles useful as pharmaceuticals such as anti-inflammatory and analgesic agents.Type: GrantFiled: February 24, 1983Date of Patent: October 21, 1986Assignee: Sumitomo Chemical Company, LimitedInventor: Michihiro Yamamoto
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Patent number: 4565817Abstract: Antitussive compounds of the formula I ##STR1## or physiologically acceptable acid addition salts thereof are disclosed, where A stands for straight or branched chain C.sub.1-5 alkylene or ##STR2## R.sub.1 stands for straight or branched chain C.sub.1-10 alkyl, halogenoalkyl, hydroxyalkyl, C.sub.5-6 cycloalkyl, vinyl, 2-ethoxyethyl, carbonylalkyl or aminoalkyl of the formula ##STR3## wherein R stands for hydrogen or methyl, n is 0 to 3,R.sub.2 stands for hydrogen or straight or branched chain alkyl,R.sub.3 stands for hydrogen or straight or branched chain alkyl or,R.sub.2 and R.sub.3 together with the nitrogen atom may form a 5-6 membered ring, which ring can optionally contain an oxygen or a second nitrogen atom, the latter, optionally substituted by methyl or,R.sub.1 can stand for a phenyl group of the formulaR.sub.4 R.sub.5 C.sub.6 H.sub.3whereinR.sub.4 and R.sub.5 represent independently hydrogen, chlorine, hydroxy, methoxy, ethoxy, methyl or amino or,R.sub.Type: GrantFiled: March 11, 1983Date of Patent: January 21, 1986Assignee: Chinoin Gyogyszer-es Vegyeszeti Termekek Gyara R.T.Inventors: Dezso Korbonits, Maria Szomor nee Wundele, Gergely Heja, Ida Szvoboda nee Kanzel, Pal Kiss, Csaba Gonczi, Endre Palosi, Gabor Kovacs, Judit Kun, Emil Minker, Sandor Virag, Gyula Sebestyen, Tamas Szuts
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Patent number: 4562186Abstract: There are disclosed novel compounds having the formula ##STR1## where X is hydrogen, halogen (F, Cl, Br or I), loweralkyl or loweralkoxy; and R is --CH, --CONH.sub.2, --COOCH(CH.sub.3).sub.2, --COOH, --COO(CH.sub.2).sub.4 Cl, ##STR2## R.sub.1 and R.sub.2 being independently hydrogen or lower alkyl and R.sub.3 being ##STR3## an optical antipode thereof or a pharmaceutically acceptable acid addition salt thereof, which are useful as antihypertensive, analgesic and antiinflammatory agents, methods for synthesizing them, and pharmaceutical compositions comprising an effective amount of such a compound.Type: GrantFiled: January 22, 1985Date of Patent: December 31, 1985Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: John J. Tegeler, Craig J. Diamond
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Patent number: 4556649Abstract: Insecticidally active novel substituted malonic acid diamide insecticides of the formula ##STR1## wherein R.sup.1 represents aryl or heteroaryl, each of which can optionally be substituted,R.sup.2 represents hydrogen or trialkylsilyl, and represents alkyl, cycloalkyl, alkenyl, alkinyl, aralkyl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulphenyl, arylsulphenyl, alkylsulphonyl, arylsulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, arylaminosulphonyl or arylalkylaminosulphonyl, each of which can optionally be substituted, and represents radicals of the formula--CO--NR.sup.5 R.sup.6whereinR.sup.5 and R.sup.6 independently of one another represent hydrogen, alkyl, cycloalkyl, aryl, alkylaminocarbonyl, arylaminocarbonyl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulphonyl or arylsulphonyl, it being possible for these radicals to be optionally substituted,R.sup.3 represents hydrogen or the radical R.sup.4,R.sup.7 and R.sup.Type: GrantFiled: December 21, 1984Date of Patent: December 3, 1985Assignee: Bayer AktiengesellschaftInventors: Herbert Salzburg, Rudolf Fauss, Kurt Findeisen, Bernhard Homeyer
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Patent number: 4548944Abstract: Compounds of the tautomeric formula ##STR1## wherein R, R.sub.1 and R.sub.2, which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 4 carbon atoms;R.sub.3 is straight or branched alkyl, optionally interrupted by heteroatoms such as oxygen, sulfur or nitrogen; straight or branched alkenyl; alkynyl; cyano; cycloalkyl or cycloaliphatic alkyl; a bicyclic group; aryl; or a heterocyclic group; orR.sub.2 and R.sub.3, together with each other and the nitrogen atoms to which they are attached, form a heterocyclic group;R.sub.4 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; andHet is a substituted or unsubstituted heterocycle containing two or three heteroatoms;tautomers thereof, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as anti-ulcerogenics.Type: GrantFiled: February 10, 1983Date of Patent: October 22, 1985Assignee: Istituto de Angeli S.p.A.Inventors: Giuseppe Bietti, Enzo Cereda, Arturo Donetti, Piero del Soldato, Antonio Giachetti, Rosamaria Micheletti
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Patent number: 4446322Abstract: This application provides a novel process for the synthesis of 3-(2-hydroxy-2-phenylethyl)-N-[(phenylamino)carbonyl]sydnonimine derivatives and novel hydrophobic and hydrophilic acyl derivatives thereof as pro-drug central nervous system stimulants.Type: GrantFiled: October 2, 1980Date of Patent: May 1, 1984Assignee: American Home Products CorporationInventor: Reinhardt P. Stein
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Patent number: 4444770Abstract: The invention relates to imidazoazole-alkenoic acid amides of Formula (I) and methods for their production. Also included in the invention are compositions containing said alkenoic acid amides and methods for the use of said alkenoic acid amides and the compositions containing them. In addition, the invention includes the intermediate carbonyl compounds of Formula (II) and the intermediate alkenoic acids of Formula (V) as well as methods for their preparation.Type: GrantFiled: May 13, 1981Date of Patent: April 24, 1984Assignee: Bayer AktiengesellschaftInventors: Horst Meyer, Harald Horstmann, Eike Moller, Bernward Garthoff
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Patent number: 4416817Abstract: Novel 3-methoxy-2-oxoazetidine derivatives, which are shown by the following formula ##STR1## wherein R.sub.1 is amino, acylated amino or protected amino, are of value as intermediates for the synthesis of useful compounds represented by the formula ##STR2## wherein R.sub.1 has the same meaning as defined above, as drugs in the treatment of bacterial infections.Type: GrantFiled: November 18, 1981Date of Patent: November 22, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Taisuke Matsuo, Michihiko Ochiai
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Patent number: 4401817Abstract: Certain carbonyl-substituted-1-sulfonylbenzimidazole compounds are useful as antiviral agents.Type: GrantFiled: April 21, 1982Date of Patent: August 30, 1983Assignee: Eli Lilly and CompanyInventors: Charles J. Paget, James W. Chamberlin, James H. Wikel
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Patent number: 4372953Abstract: Tetrazole derivatives of the formula: ##STR1## wherein R.sup.1 is a lower alkykl, phenyl or a group of the formula: --S(O).sub.l --A--(X).sub.m --R.sup.3, and R.sup.2 is hydrogen, a lower alkyl, phenyl or a cycloalkyl when R.sup.1 is the group --S(O).sub.l --A--(X).sub.m --R.sup.3, or R.sup.2 is a group of the formula: --B--CO--R.sup.4 when R.sup.1 is a lower alkyl or phenyl and a pharmaceutically acceptable salt thereof, which have prophylactic or therapeutic activities against peptic and/or duodenal ulcers and are useful as an anti-ulcer drug; processes for the preparation of the tetrazole derivatives; and pharmaceutical composition containing said tetrazole derivatives.Type: GrantFiled: February 27, 1981Date of Patent: February 8, 1983Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Minoru Uchida, Takao Nishi, Kazuyuki Nakagawa
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Patent number: 4356178Abstract: Pharmacologically-valuable 3,4-(bis-substituted)-1,2,5-oxdiazole 2-oxides of formula I ##STR1## [wherein R denotes --NHR.sup.1, --NR.sup.2 R.sup.3, --NHR.sup.4 OR.sup.2, --NHR.sup.5 COR.sup.6 or ##STR2## R.sup.1 denotes alkyl having from 1 to 6 C atoms or cycloalkyl having 4 to 7 ring C atoms, R.sup.2 and R.sup.3 denote alkyl having from 1 to 4 C atoms, R.sup.4 denotes an alkylene radical of the formula --C.sub.n H.sub.2n --(wherein n denotes 2, 3 or 4), R.sup.5 denotes an alkylene radical of the formula --C.sub.m H.sub.2m -- (wherein m denotes 1, 2 or 3), R.sup.6 denotes --OR.sup.2, --NHR.sup.1, --NR.sup.2 R.sup.3 or --NH.sub.2, X denotes --(CH.sub.2).sub.p --, --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 -- or ##STR3## and p is 4, 5 of 6] and their pharmacologically-acceptable acid-addition compounds are prepared by elimination of hydrogen chloride from a hydroxamoyl chloride of the formulaR--CO--C(Cl).dbd.NOH (II)and dimerization.Type: GrantFiled: December 18, 1981Date of Patent: October 26, 1982Assignee: Cassella AktiengesellschaftInventors: Karl Schonafinger, Rudi Beyerle, Anton Mogilev, Helmut Bohn, Melitta Just, Piero A. Martorana, Rolf-Eberhard Nitz
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Patent number: 4324897Abstract: The disclosed [[2-(substituted amino)-2-phenylethyl]-nitrosoamino]acetonitrile derivatives and the ring closed oxadiazolium salts thereof as well as their pharmaceutically acceptable acid addition salts are antihypertensive agents useful in the treatment of hypertension.Type: GrantFiled: May 18, 1981Date of Patent: April 13, 1982Assignee: American Home Products CorporationInventor: Reinhardt P. Stein
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Patent number: 4301285Abstract: This application provides a novel process for the synthesis of 3-[1(hydroxymethyl)-2-phenylethyl]-N-[(phenylamino)carbonyl]sydnonimine derivatives and novel hydrophobic and hydrophilic acyl derivatives thereof as pro-drug central nervous system stimulants.Type: GrantFiled: October 2, 1980Date of Patent: November 17, 1981Assignee: American Home Products CorporationInventor: Reinhardt P. Stein
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Patent number: 4293462Abstract: The invention concerns a process for the manufacture of 7.beta.-amino-3-cephem-3-ol-4-carboxylic acid compounds by ring closure of esters of 2-[4-(substituted-thio)-3-acylamino-2-oxoazetidin-1-yl]-3-substituted-amin o-crotonic acids and solvolyzing the enamino group in the resulting 7.beta.-acylamino-3-substituted-amino-cephem-4-carboxylic acid esters.Type: GrantFiled: December 10, 1979Date of Patent: October 6, 1981Assignee: Ciba-Geigy CorporationInventors: Robert B. Woodward, Hans Bickel
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Patent number: 4289885Abstract: A compound of the formula: ##STR1## in which R.sup.1 and R.sup.2 are, independently, hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo, perfluoroalkyl of 1 to 3 carbon atoms, nitro, alkanoyl of 2 to 4 carbon atoms or alkoxycarbonyl of 2 to 4 carbon atoms;R.sup.3 is hydrogen, halo, nitro or alkanoyl of 2 to 4 carbon atoms;R.sup.4 is hydrogen, halo, nitro or perfluoroalkyl of 1 to 3 carbon atoms;R.sup.5 and R.sup.6 are, independently, hydrogen or methyl; andR.sup.7 and R.sup.8 are, independently, alkyl of 1 to 4 carbon atoms, or when taken with the nitrogen atom to which they are attached form a piperidinyl, pyrolidinyl, morpholinyl, N-alkyl piperazinyl in which the alkyl group contains from 1 to 6 carbon atoms or N-phenylpiperazinyl group ora non-toxic acid addition salt thereof, are central nervous system stimulants.Type: GrantFiled: October 2, 1980Date of Patent: September 15, 1981Assignee: American Home Products CorporationInventor: Reinhardt P. Stein