The Five-membered Hetero Ring Is Unsubstituted Or Alkyl Substituted Only (e.g., Pyrrole, Etc.) Patents (Class 548/564)
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Patent number: 5907044Abstract: A method of isolating 1-?N.sup.2 -((S)-ethoxycarbonyl)-3-phenylpropyl)-N.sup.6 -trifluoroacetyl!-L-lysyl-L-proline (lisinopril (TFA) ethyl ester, LPE). The solvent or solvent mixture used for the extraction is also a main constituent of the solvent or solvent mixture from which the crystallization takes place. High yield as well as good purity of the end product are obtained, without distillation. 1-?N.sup.2 -((S)-ethoxycarbonyl)-3-phenylpropyl)-N.sup.6 -trifluoroacetyl!-L-lysyl-L-proline (lisinopril (TFA) ethyl ester, LPE) is described as a precursor for producing an ACE inhibitor.Type: GrantFiled: October 16, 1997Date of Patent: May 25, 1999Assignee: Degussa AktiengellschaftInventors: Matthias Kottenhahn, Roland Moller, Michael Kraft, Karlheinz Drauz, Klaus Stingl
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Patent number: 5883106Abstract: Novel compounds having the ability to inhibit 5-lipoxygenase enzyme and having the following formula I: ##STR1## and the pharmaceutically acceptable salts thereof, wherein Ar.sup.1 is a heterocyclic moiety which is selected from imidazolyl, pyrrolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, indolyl, indazolyl and benzimidazolyl, which is bonded to X.sup.1 through a ring nitrogen atom, and which may be optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, and C.sub.1-4 alkyl; X.sup.1 is a direct bond or C.sub.1-4 alkylene; Ar.sup.2 is phenylene optionally substituted with halo, hydroxy, cyano, and amino X.sup.2 is --A--X-- or --X--A-- wherein A is a direct bond or C.sub.1-4 alkylene and X is oxy, thio, sulfinyl or sulfonyl; Ar.sup.3 is phenylene, pyridylene, thienylene, furylene, oxazolylene or thiazolylene optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino and C.sub.1-4 alkyl; R.sup.1 and R.sup.2 are each C.sub.Type: GrantFiled: February 6, 1998Date of Patent: March 16, 1999Assignee: Pfizer Inc.Inventors: Rodney W. Stevens, Takashi Mano, Kazunari Nakao, Yoshiyuki Okumura
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Patent number: 5869696Abstract: Universal solid support oligonucleotide synthesis reagents, oligonucleotide synthesis processes, and reagents for cleaving oligonucleotides from solid supports are disclosed. Oligonucleotide synthesis reagents have the following general formula:SS--R.sup.6 --O--R.sup.3 Iwherein SS is a solid support; R.sup.6 is ##STR1## where R.sup.5 is hydrogen or alkyl and R.sup.4 is a phosphate protecting group; and R.sup.3 is a ring moiety having vicinal groups --XR.sup.1 and --YR.sup.2 wherein each of X and Y is independently selected from the group consisting of O, S and NH and one of R.sup.1 and R.sup.2 is a blocking moiety and the other is hydrogen or a hydroxy protecting group. Oligonucleotide cleaving reagents include methylamine and/or ammonium hydroxide and trimethylamine.Type: GrantFiled: April 22, 1996Date of Patent: February 9, 1999Assignee: Beckman Instruments, Inc.Inventors: M. Parameswara Reddy, Maged A. Michael, Firdous Farooqui
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Patent number: 5817691Abstract: There are provided arylthio, -sulfinyl and -sulfonyl pyrrole compounds having the structural formula I ##STR1## Further provided are compositions and methods comprising those compounds for the control of insects.Type: GrantFiled: April 9, 1997Date of Patent: October 6, 1998Assignee: American Cyanamid CompanyInventors: Keith Douglas Barnes, Robert Eugene Diehl, Susan Hensen Trotto, Yulin Hu
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Patent number: 5792778Abstract: The present invention addresses 2-substituted aryl pyrroles, as well as compositions containing such compounds and methods of treatment. Cytokine mediated diseases refers to diseases or conditions in which excessive or unregulated production or activity of one or more cytokines occurs. Interleukin-1 (IL-1), Interleukin-6 (IL-6), Interleukin-8 (IL-8) and Tumor Necrosis Factor (TNF) are cytokines which are involved.Type: GrantFiled: August 8, 1996Date of Patent: August 11, 1998Assignee: Merck & Co., Inc.Inventors: Stephen E. de Laszlo, Nigel J. Liverton, Gerald S. Ponticello, Harold G. Selnick, Nathan B. Mantlo
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Patent number: 5773660Abstract: A process for preparing amines of the formula I ##STR1## where R.sup.1,R.sup.2,R.sup.3,R.sup.4,R.sup.5 and R.sup.6 are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -alkylaryl or C.sub.7 -C.sub.20 -aralkyl,R.sup.1 and R.sup.2 are together a saturated or unsaturated C.sub.3 -C.sub.9 -alkylene dichain, andR.sup.3 or R.sup.5 is C.sub.21 -C.sub.200 -alkyl or C.sub.21 -C.sub.200 -alkenyl or together they are a C.sub.2 -C.sub.12 -alkylene dichain,by reacting olefins of the formula II ##STR2## where R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each as defined above, with ammonia or primary or secondary amines of the formula III ##STR3## where R.sup.1 and R.sup.2 are each as defined above, at temperatures from 200.degree. to 350.degree. C.Type: GrantFiled: January 21, 1997Date of Patent: June 30, 1998Assignee: BASF AktiengesellschaftInventors: Karsten Eller, Rudolf Kummer, Eugen Gehrer
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Patent number: 5691337Abstract: Oxy-phenyl-(phenyl)glycinolamides with heterocyclic substituents are prepared by reaction of the corresponding oxyphenylcarboxylic acids with heterocyclic substituents with phenylglycinol. The new substances are suitable as active compounds in medicaments, in particular in agents having an antiatherosclerotic action.Type: GrantFiled: January 13, 1997Date of Patent: November 25, 1997Assignee: Bayer AktiengesellschaftInventors: Ulrich Muller, Richard Connell, Siegfried Goldmann, Klaus-Helmut Mohrs, Siegfried Raddatz, Michael Matzke, Rudi Grutzmann, Martin Beuck, Stefan Wohlfeil, Hilmar Bischoff, Dirk Denzer
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Patent number: 5502213Abstract: A process for purifying crude pyrroles obtained in the preparation of pyrroles of the general formula I ##STR1## where R is hydrogen or a C.sub.1 -C.sub.6 -alkyl radical, which comprises treating the mixture containing the crude pyrrole with an acid or an activated carboxylic acid derivative and removing the pyrrole from the mixture by distillation at reduced pressure and at a bottom temperature of up to 160.degree. C.Type: GrantFiled: January 21, 1994Date of Patent: March 26, 1996Assignee: BASF AktiengesellschaftInventors: Peter Pfab, Peter Wahl, Dieter Franz
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Patent number: 5422335Abstract: A herbicidal composition containing one or more substituted 2-aminothiophenes of the formula I ##STR1## where R.sup.1 and R.sup.2 together from a C.sub.4 -alkylene chain to which a benzene ring may be fused,R.sup.3 is --CN or CX--R.sup.6, where R.sup.6 is hydroxyl, C.sub.1 -C.sub.4 -alkoxy or amino,R.sup.4 is hydrogen or a phenyl group which may carry one or two nitro radicals,--PO(OR.sup.8).sub.2, --CX--R.sup.9, --SO.sub.2 R.sup.10, --CX--N(H) --CO--R.sup.8 or --CX--N(R.sup.7)--SO.sub.2 --R.sup.11,whereR.sup.8 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl groupR.sup.9 is C.sub.1 -C.sub.20 -alkyl, partially or completely halogenated C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.6 -cycloalkyl, or amino, C.sub.1 -C.sub.4 -alkylamino, C.sub.3 -C.sub.8 -cycloalkylamino, phenyl or phenylamino, where the aromatic moiety may carry at least one of nitro and halogen;R.sup.10 is C.sub.1 -C.sub.4 -alkyl or phenyl, which may carry one C.sub.1 -C.sub.4 -alkyl radical;R.sup.Type: GrantFiled: June 7, 1993Date of Patent: June 6, 1995Assignee: BASF AktiengesellschaftInventors: Helmut Hagen, Gerhard Nilz, Helmut Walter, Andreas Landes
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Patent number: 5367084Abstract: A process for preparation of new or previously known pyrrol derivatives is provided. The process involves reacting a nitroalkane or a nitroalkene with an isocyanoacetate in the presence of a proprophosphatrane "super base" to prepare the pyrrol compounds. Through production of new pyrrol compounds, new pyrrol derivatives such as dipyrromethane and porphyrin may be synthesized. In addition, the high yields of pyrrol compounds produced according to the method of the invention provide for more efficient production of previously known dipyrromethane and porphyrin compounds. The invention further provides a mild, high yield process for de-esterification of esterified pyrrol and dipyrromethane compounds. The invention also provides a synthetic method for the production of high yields of oxazoles through reaction of an aryl halide or acid anhydride with an isocyanoacetate in the presence of a prophosphatrane "super base".Type: GrantFiled: October 26, 1993Date of Patent: November 22, 1994Assignee: Iowa State University Research Foundation, Inc.Inventors: John Verkade, Jiansheng Tang
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Patent number: 5132307Abstract: New tetralin derivatives of the formula I ##STR1## wherein R.sup.1 to R.sup.8 and Z have the meanings indicated herein and salts thereof, exhibit an effect on the cardiovascular system.Type: GrantFiled: November 7, 1989Date of Patent: July 21, 1992Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Manfred Baumgarth, Rolf Gericke, Rolf Bergmann, Jacques De Peyer, Ingeborg Lues
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Patent number: 5118704Abstract: Optically active or racemic compounds are provided having the formula ##STR1## where R.sub.2, R.sub.3, R.sub.4 and R.sub.6 are defined in the specification; R.sub.1 is selected from the group consisting of ##STR2## wherein Y is selected from the group consisting of hydroxy, nitro, cyano, azido, amino, acylamino, carboxyamido, trifluoromethyl, sulfate, sulfonamido, halogen, hydrocarbyl and hetero atom-substituted hydrocarbyl radicals, wherein said heteroatoms are selected from the group consisting of halogen, nitrogen, oxygen, sulfur and phosphorus and said hydrocarbyl radicals comprise from 1 to 12, preferably 1 to 6, carbon atoms, and a is an integer of from zero to 3, for instance zero to 2; and pharmaceutically acceptable salts thereof; as dopaminergics.Type: GrantFiled: September 11, 1991Date of Patent: June 2, 1992Assignee: Whitby Research, Inc.Inventors: Gevork Minaskanian, James V. Peck
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Patent number: 5086074Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable salt thereof, wherein R.sup.2 is selected from hydroxy and lower alkoxy, R.sup.5 is lower alkyl, and R.sup.11 and R.sup.12 are independently selected from hydrogen, halo, hydroxy, methoxy, and lower alkyl, are selective .alpha..sub.2 adrenergic receptor antagonists useful in the treatment of glaucoma.Type: GrantFiled: March 26, 1990Date of Patent: February 4, 1992Assignee: Abbott LaboratoriesInventors: John F. DeBernardis, Robert E. Zelle, Fatima Z. Basha
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Patent number: 4906758Abstract: Pyrroles of the formula I ##STR1## are prepared by a process in which a dialkoxytetrahydrofuran of the formula II ##STR2## where R.sup.2 to R.sup.5 in the formulae (I) and (II) are identical or different and are each hydrogen, a straight-chain or branched alkyl or alkenyl radical of not more than 12 carbon atoms, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl or aralkyl radical of 6 to 16 carbon atoms, and two non-adjacent radicals R.sup.6 to R.sup.9 are alkoxy and the other two radicals R.sup.6 to R.sup.9 are hydrogen, is reacted with ammonia or a primary amine H.sub.2 NR.sup.1, where R.sup.1 in formula (I) is hydrogen, alkyl, aryl, alkylaryl, aralkyl or cycloalkyl, in the presence of an acidic, solid, heterogeneous catalyst. Zeolites, for example those of the pentasil type or faujasite type, or phosphates, acidic oxides, phosphoric acid or boric acid on a carrier can be used as the solid heterogeneous catalysts.Type: GrantFiled: August 12, 1988Date of Patent: March 6, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Michael Hesse, Hardo Siegel
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Patent number: 4863522Abstract: A composition comprising(a) a dianthraquinonyl pigment of formula I ##STR1## (b) a compound of formula II ##STR2## wherein X.sup..sym. is H.sup..sym. or a group of formula M.sup.n.sym. /n or N.sup..sym. (R)(R.sub.1)(R.sub.2)(R.sub.3), M.sup.n.sym. is a monovalent metal cation of valency n, n is 1, 2 or 3, each of R, R.sub.1, R.sub.2 and R.sub.3 independently is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl or phenyl which is substituted by C.sub.1 -C.sub.18 alkyl, or R.sub.2 and R.sub.3, together with the linking nitrogen atom, are a pyrrolidine, imidazolidine, piperidine, piperazine or morpholine radical, or R.sub.1, R.sub.2 and R.sub.3, together with the linking nitrogen atom, are a pyrrole, pyridine, picoline, pyrazine, quinoline or isoquinoline radical, r and t are each independently of the other 0 or 1, with the proviso that at least one of r and t must be 1.Type: GrantFiled: December 22, 1987Date of Patent: September 5, 1989Assignee: Ciba-Geigy CorporationInventors: Max Jost, Edward E. Jaffe, Philippe Bugnon
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Patent number: 4798894Abstract: Compounds containing at least one N,N-dialkylatable amino or amido group (e.g., aniline, dodecylamine, acetamide) are converted in a highly efficient manner into gem cyclodialkylated compounds by reaction with an unstrained cyclic ether (e.g., tetrahydrofuran) or a polyol (e.g., 1,4-butane diol) cyclizable to an unstrained ether using titanium dioxide catalysts that have prior to use:(1) a surface area of at least 70 square meters per gram (as determined by the BET method), and(2) the capability of chemically adsorbing at 100.degree. C. at least 35.times.10.sup.4 millimoles of gaseous ammonia per square meter of surface area.Type: GrantFiled: May 11, 1987Date of Patent: January 17, 1989Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4762929Abstract: Saturated nitrogen-containing five-membered and six-membered heterocycles are aromatized by dehydrogenation in the gas phase in the presence of a supported palladium catalyst containing an alkaline earth metal halide, at from 150.degree. to 350.degree. C. and under from 0.1 to 10 bar.Type: GrantFiled: June 4, 1987Date of Patent: August 9, 1988Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4668691Abstract: 1-Oxo-1,3,4,7-tetrahydrobenzofuranes of the formula ##STR1## in which X is O or S,R is optionally substituted phenyl or heteroaryl,R.sup.1 is OH, monoalkylamino or dialkylamino, andR.sup.2 is an acyl or esterified carboxy radical, or pharmacologically acceptable salts thereof, which are active in circulation, e.g. they increase myocardial contractility, increase the flow of Ca.sup.2+ into the cell, increase blood pressure, reduce blood sugar, reduce swelling of mucous membranes and affect the salt and/or fluid balance.Type: GrantFiled: April 18, 1985Date of Patent: May 26, 1987Assignee: Bayer AktiengesellschaftInventors: Siegfried Goldmann, Matthias Schramm, G/u/ nter Thomas, Rainer Gross
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Patent number: 4626592Abstract: Amines and amides are N,N-cyclodialkylated by reaction with an unstrained cyclic ether in the presence of a B-subgroup metal oxide alkylation catalyst, preferably a Group IV-B metal oxide such as titanium dioxide.Type: GrantFiled: December 24, 1984Date of Patent: December 2, 1986Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4582575Abstract: Electrically conductive composites comprising a dielectric porous substance, e.g. fiberglass fabric, and a pyrrole polymer deposited in the pores of such substance. The composites are produced by contacting the porous substance with an anode in an electrolytic cell containing an electrolyte comprising a pyrrole monomer and a substantially non-nucleophilic anion such as bisulfate, and passing an electric current through the cell, thus electrochemically precipitating a conductive pyrrole polymer in the pores of such substance.Type: GrantFiled: September 4, 1984Date of Patent: April 15, 1986Assignee: Rockwell International CorporationInventors: Leslie F. Warren, Dean S. Klivans, Louis Maus
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Patent number: 4560769Abstract: Pyrroles are prepared by a process in which ammonia or an amine is reacted with a but-2-ene-1,4-diol in the presence of a supported catalyst containing copper, silver, zinc, palladium, nickel, cobalt and/or platinum and/or compounds of these metals as catalytic materials, and in the presence or absence of compounds of chromium and/or manganese as additional catalysts, in the gas phase.The pyrroles obtainable by the process of the invention are useful starting materials for the preparation of dyes, corrosion inhibitors, drugs and pesticides.Type: GrantFiled: March 9, 1984Date of Patent: December 24, 1985Assignee: BASF AktiengesellschaftInventors: Helmuth Menig, Martin Fischer, Karl Baer
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Patent number: 4548724Abstract: Dispersant additives in lubricating oils are formed by reaction of polyacids such as 1,3,6-hexane tricarboxylic acid and polyisobutenyl succinimide of a polyamine.Type: GrantFiled: May 29, 1984Date of Patent: October 22, 1985Assignee: Texaco Inc.Inventors: Thomas J. Karol, Rodney L. Sung, Benjamin J. Kaufman
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Patent number: 4521602Abstract: A pyridine or a pyrrole is obtained in a one-stage process directly from an .alpha.,.omega.-dinitrile of appropriate carbon skeleton when the dinitrile is reacted in the gas phase with hydrogen, over a hydrogenation catalyst.Type: GrantFiled: June 9, 1983Date of Patent: June 4, 1985Assignee: BASF AktiengesellschaftInventors: Walter Rebafka, Gerd Heilen, Klaus Halbritter, Wolfgang Franzischka
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Patent number: 4485243Abstract: A process is described for the catalytic gas phase reduction of 4-oxoalkanenitriles to form 2-alkylpyrroles in high yields and conversions.Type: GrantFiled: June 1, 1982Date of Patent: November 27, 1984Assignee: Stamicarbon B.V.Inventors: Roland E. van der Stoel, Petrus H. J. Janssen, Cornelis G. M. van de Moesdijk
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Patent number: 4465678Abstract: Aminopropiophenone derivatives of the formula ##STR1## in which X is a keto group or an oxime radical of the formula>C.dbd.N--O--R.sup.4,Y each independently is an alkyl radical, a halogen atom, or a halogenoalkyl, alkoxy, alkythio, halogenoalkoxy, halogenoalkylthio, cycloalkyl or cyano radical,n is 0, 1, 2, or 3,R.sup.1 and R.sup.2 each independently is an alkyl radical, or,R.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, complete an optionally substituted heterocyclic radical of the formula ##STR2## or in addition, if X is >C.dbd.N--O--R.sup.4, also may complete an optionally substituted heterocyclic radical of the formula ##STR3## R.sup.3 is a hydrogen atom or an alkyl radical, and R.sup.4 is a hydrogen atom or an alkyl, alkenyl, alkinyl or aralkyl radical,or physiologically acceptable acid addition salts thereof, which possess fungicidal activity.Type: GrantFiled: November 24, 1982Date of Patent: August 14, 1984Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Knops, Wolfgang Kramer, Paul-Ernst Frohberger
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Patent number: 4417048Abstract: Organonitrogen compounds bearing a labile hydrogen atom directly bonded to a reactive nitrogen function, e.g., nitrogen heterocycles or substituted anilines, are N-alkylated with an N-alkylating agent in the presence of inorganic base and at least one sequestering agent having the structural formula:N--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (I)wherein n is a number ranging from 0 to 10, R.sub.1, R.sub.2, R.sub.3, R.sub.4, which may be identical or different, each represents a hydrogen atom or an alkyl radical having 1 to 4 carbon atoms, and R.sub.5 represents an alkyl or cycloalkyl radical having 1 to 12 carbon atoms, a phenyl radical, or a radical of the formula --C.sub.m H.sub.2m --.phi., or C.sub.m H.sub.2m+1 --.phi.--, m ranging from 1 to about 12 and .phi. being phenyl.Type: GrantFiled: February 24, 1982Date of Patent: November 22, 1983Assignee: Rhone-Poulenc Specialties ChimiquesInventors: Gerard Soula, Maurice Balme
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Patent number: 4401545Abstract: Electrically conductive complexes of polypyrroles with nitroaromatic anions are prepared by polymerizing pyrrole, an N-alkylpyrrole and/or an N-arylpyrrole by anodic oxidation in a polar solvent, in the presence of a salt of an acidic nitroaromatic compound.Type: GrantFiled: December 21, 1981Date of Patent: August 30, 1983Assignee: BASF AktiengesellschaftInventors: Herbert Naarmann, Dieter Naegele, Klaus Penzien, Johannes Schlag, Volker Kiener, Hugo Boehm
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Patent number: 4374991Abstract: This invention relates to a method of using compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl or alkenyl; R.sup.2 is hydrogen, alkyl, cycloalkyl or mononuclear aryl or R.sup.1 and R.sup.2, taken together with the carbon atom to which they are attached, form a cycloalkyl or cycloalkoxyalkyl; R.sup.3 is hydroxy, alkyl, alkoxycarbonyl, hydroxy lower alkyl or a radical of the formula: --C(.dbd.Y)NR.sup.4 R.sup.5 wherein R.sup.4 is hydrogen, alkyl, alkenyl, R.sup.5 is alkyl, alkenyl, alkoxyalkyl, carbalkoxy, mononuclear aryl, or R.sup.4 and R.sup.5 may be joined together with the nitrogen atom to which they are attached to form a 5 to 7 membered heterocyclic ring having from 1 to 3 hetero atoms; Y is O or S; X is alkyl, alkoxycarbonylalkyl or cyano; m is an integer of 0 to 2 and n and n' are integers each having a value of 1 to 2 and the dotted line indicates an optional double bond anywhere in the ring, compositions containing said compounds as insect repellents and to novel compounds.Type: GrantFiled: December 29, 1981Date of Patent: February 22, 1983Assignee: Rohm and Haas CompanyInventor: Joel R. Smolanoff
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Patent number: RE32896Abstract: Amines and amides are N,N-cyclodialkylated by reaction with an unstrained cyclic ether in the presence of a B-subgroup metal oxide alkylation catalyst, preferably a Group IV-B metal oxide such as titanium dioxide.Type: GrantFiled: March 23, 1987Date of Patent: March 28, 1989Assignee: Ethyl CorporationInventor: Duane C. Hargis