Chalcogen Attached Indirectly To The Five-membered Hetero Ring By Acyclic Nonionic Bonding Patents (Class 548/562)
-
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
-
Patent number: 5359090Abstract: There is provided a safe and effective means of introducing an alkoxymethyl group onto the ring Nitrogen atom of a wide variety of pyrrole compounds via the reaction of the appropriate pyrrole precursor sequentially with dialkoxymethane, Vilsmeier reagent and a tertiary amine. The product 1-(alkoxymethyl)pyrroles are useful as insecticidal, acaricidal, nematocidal and molluscicidal agents.Type: GrantFiled: December 29, 1993Date of Patent: October 25, 1994Assignee: American Cyanamid CompanyInventors: Robert F. Doehner, Jerry M. Barton
-
Patent number: 5354862Abstract: Antimicrobial compounds of the formula ##STR1## wherein R is selected from (A)(C.sub.1 to C.sub.20) straight or branched alkyl, optionally substituted with hydroxy, halogen, alkoxy, phenoxy, or --C(.dbd.O)R' wherein R' is selected from C.sub.1 -C.sub.20)alkyl, (C.sub.1 -C.sub.20)alkoxy, phenoxy, or NHR" wherein R" is (C.sub.1 -C.sub.6)alkyl or phenyl; (B) benzyl; (C) phenethyl; (D) cyanoethyl; (E) 2-cyanoethyl; (F) propargyl; and (G) allyl;X=halogen (chlorine, bromine, or iodine), phosphate, acetate, benzoate, citrate, tartrate, alkyl- or aryl-sulfonate, alkylsulfate; and ##STR2## represents a 3-to 7-membered ring that contains at least one nitrogen atom optionally substituted with one or more substituents selected from (C.sub.1 -C.sub.3)alkyl, halo, and carboxyl, said ring optionally containing one or two hetreoatoms in addition to said one nitrogen atom, selected from sulfur, oxygen, and a second nitrogen;Processes for inhibiting microbial growth, and compositions suitable therefore are also disclosed.Type: GrantFiled: August 31, 1993Date of Patent: October 11, 1994Assignee: Rohm and Haas CompanyInventor: Adam C. Hsu
-
Patent number: 5352820Abstract: The invention is an expedient route to synthesizing substituted or unsubstituted aryl-2-propenoic esters. The substituted or unsubstituted aryl-2-propenoic esters are useful in preparing optically active substituted or unsubstituted 2-arylpropanoic acids known to be active anti-inflammatory agents.Type: GrantFiled: June 28, 1993Date of Patent: October 4, 1994Inventor: Jeremy I. Levin
-
Patent number: 5340835Abstract: A compound selected from the group consisting of all stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein Y and Z are individually selected from the groups consisting of hydrogen, halogen, --CF.sub.3, alkyl, alkoxy and alkylthio of 1 to 8 carbon atoms and aryl, aryloxy and arylthio of up to 14 carbon atoms optionally substituted with at least one member of the group consisting of halogen, hydroxy optionally esterified etherified, --CF.sub.3 and alkyl of 1 to 8 carbon atoms and R is alkyl of 1 to 8 carbon atoms or the remainder of a pyrethrinoid alcohol having excellent pesticidal properties and their preparation and intermediates.Type: GrantFiled: January 19, 1993Date of Patent: August 23, 1994Assignee: Roussel-UCLAFInventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute, Fabienne Pilorge, Nicole Reinier
-
Patent number: 5330981Abstract: This application describes 3-arylalkyl esters of 4,5-dihydro-9,10-dioxo-2-anthracenecarboxylic acid and a process for making them. Also described is a method of using the compounds in the treatment of arthritis.Type: GrantFiled: December 30, 1992Date of Patent: July 19, 1994Assignee: Istituto Gentili S.p.A.Inventors: Sergio Rosini, Maurizio Mian
-
Patent number: 5326911Abstract: Ortho-amides of the formula ##STR1## can be prepared by reacting salts of the formula ##STR2## with alcoholates of the formulaM.sup.1 OR.sup.1 (III)where the radicals R.sup.1 to R.sup.4, M.sup.1 and X.sup..crclbar. have the meaning given in the description. The alcoholates are employed in highly active form with an effective content of 98-100% M.sup.1 OR.sup.1.Type: GrantFiled: July 20, 1992Date of Patent: July 5, 1994Assignee: Bayer AktiengesellschaftInventors: Heinz-Ulrich Blank, Helmut Kraus, Gerhard Marzolph, Nikolaus Muller
-
Patent number: 5310938Abstract: This invention relates to methods and compositions for treating, controlling, preventing and protecting warm-blooded animals from infestation and infection by helminths, acarids and arthropod endo- and ectoparasites by administering or applying to the animals a substituted arylpyrrole compound.Type: GrantFiled: July 13, 1993Date of Patent: May 10, 1994Assignee: American Cyanamid CompanyInventors: Dale G. Brown, Robert E. Diehl, Donald P. Wright, Jr., Jack K. Siddens, deceased
-
Patent number: 5300508Abstract: A method for intercepting an activated species of dioxygen by administering an N-substituted pyrrole derivative having the formula: ##STR1## in which: R is an amino acid derivative, a non-protein peptide, an amino sugar processing a free primary amino group, a purine bases which is substituted, at position 9 by alkyl groups, or a pyrimidine bases possessing a free primary amino group, wherein the pyrimidine bases are substituted by at least one SH group; R.sub.1 represents one or more substituents, identical or different and are a hydrogen, an alkyl radical containing from 1 to 6 carbon atoms, a primary amino radical, a secondary amino radical NHB, or a tertiary amino radical--N(B,B'), wherein B and B', identical or different represent an alkyl group of 1 to 6 carbon atoms, a SH or SB radical, wherein B is defined above, a --CH.sub.Type: GrantFiled: January 31, 1992Date of Patent: April 5, 1994Assignee: Centre National de la Recherche ScientifiqueInventors: Alain Valla, Michel Giraud, Marc Bazin, Rene Santus
-
Patent number: 5286743Abstract: There are provided N-aminoalkylcarbonyloxyalkylpyrrole compounds of formula I ##STR1## and their use for the control of insects, acarina and mollusks. Further provided are compositions and methods comprising those compounds for the protection of plants from attack by insects, acarina and mollusks.Type: GrantFiled: October 27, 1992Date of Patent: February 15, 1994Assignee: American Cyanamid CompanyInventors: David G. Kuhn, Stephen F. Donovan, Joseph A. Furch
-
Patent number: 5286741Abstract: There are provided N-oxy- and thioalkylcarbonyloxyalkylpyrrole compounds of formula I and their use for the control of insects, acarina and mollusks. Further provided are compositions and methods comprising those compounds for the protection of plants from attack by insects, acarina and mollusks.Type: GrantFiled: October 27, 1992Date of Patent: February 15, 1994Assignee: American Cyanamid CompanyInventors: David G. Kuhn, Stephen F. Donovan, Joseph A. Furch
-
Patent number: 5281719Abstract: Bis- and tris(trifluoromethyl)arylpyrrole compounds which are effective for the control of insects and acarids are described. A method for the insecticidal and acaricidal use of said compounds and methods for the preparation of said compounds are presented.Type: GrantFiled: April 23, 1993Date of Patent: January 25, 1994Assignee: American Cyanamid CompanyInventors: Venkataraman Kameswaran, Victor M. Kamhi
-
Patent number: 5278184Abstract: Antirhinoviral compounds having the formula ##STR1## wherein R is hetrocyclic, particularly pyrrole or pyrrolidine, X is H.sub.2 or O, n IS 3 to 7, and R.sub.1 is substituted phenyl are disclosed.Type: GrantFiled: April 17, 1992Date of Patent: January 11, 1994Assignee: Repla Chemical Ltd.Inventors: Marino Artico, Federico Corelli, Silvio Massa, Antonello Mai, Enzo Tramontano
-
Patent number: 5278295Abstract: A pyrrole polymer membrane having electrical conductivity and liquid crystal properties in the same matrix. The starting pyrrole monomer derivative is illustrated by the formula ##STR1## where R.sub.1 and R.sub.2 are selected so that at least either of them is an electron attractive group. Methods of producing such membranes by a electropolymerization process and by a chemical oxidation process are described.Type: GrantFiled: May 7, 1992Date of Patent: January 11, 1994Assignee: Nippon Soda Co., Ltd.Inventors: Hirofumi Suzuki, Takehira Kaneko, Nobuo Matsui, Isami Hamamoto, Tetsuya Katoh, Toshiaki Satoh, Fuminiko Nagasaki
-
Patent number: 5258382Abstract: Tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3'-pyrrolidine derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, trifluoromethyl, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, or nitro, and R.sup.3 is hydrogen, halogen or alkyl having 1 to 6 carbon atoms, and pharmaceutically acceptable salts thereof, processes for preparation thereof, and pharmaceutical composition containing the same. Said compounds and their salts show excellent aldose reductase inhibitory activity and are useful for the prevention and treatment of diabetic complications.Type: GrantFiled: June 19, 1992Date of Patent: November 2, 1993Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Toshiyuki Negoro, Makoto Murata, Shozo Ueda, Buichi Fujitani, Yoshiyuki Ono
-
Patent number: 5256796Abstract: There is provided a method for the preparation of 2-aryl-5-trifluoromethylpyrrole compounds via the reaction of an appropriate haloenamine and alkyl trifluoroacetoacetate. The pyrrole compounds produced are useful as insecticidal, acaricidal and nematocidal agents and as intermediates in the manufacture of said agents.Type: GrantFiled: December 11, 1992Date of Patent: October 26, 1993Assignee: American Cyanamid CompanyInventor: Venkataraman Kameswaran
-
Patent number: 5254713Abstract: Novel 2- or 3-chloropyrroles represented by the general formula: ##STR1## wherein R.sup.1 represents hydrogen atom, chlorine atom, alkyl group, or aryl group which may optionally be substituted, with the proviso that any one of the two groups represented by R.sup.1 is chlorine atom,R.sup.2 represents alkyl group or aryl group which may optionally be substituted, andR.sup.3 represents tertiary alkyl group which may be substituted by phenyl, or phenyl which may optionally be substituted, andprocesses for preparing the same.Type: GrantFiled: February 10, 1993Date of Patent: October 19, 1993Assignee: Nihon Bayer Agrochem K.K.Inventors: Shinzo Kagabu, Itsumi Kawai, Katsuaki Wada
-
Patent number: 5254559Abstract: There are provided 1-(substituted)thioalkylpyrrole compounds of formula I ##STR1## the use thereof for the control of insect, acarid and mollusk pests and methods and compositions for the protection of crops from the ravages of said pests.Type: GrantFiled: December 4, 1991Date of Patent: October 19, 1993Assignee: American Cyanamid CompanyInventors: David G. Kuhn, Venkataraman Kameswaran
-
Patent number: 5250546Abstract: Amino-alcohol derivatives of the formula, ##STR1## where R.sub.1 is a straight or branched alkyl group having 3 to 8 carbon atoms, R.sub.2 and R.sub.3 are each a lower alkyl group, or R.sub.2 and R.sub.3 form a 5- to 7-membered ring together with the adjacent nitrogen atom which may have an oxygen atom attached thereto, R.sub.4 is a hydrogen atom or a lower alkyl group, R.sub.5 is a hydrogen atom or a lower alkyl group, X is a hydrogen or halogen atom or a lower alkyl or lower alkoxy group, and n is an integer of 2 or 3, and acid addition salts thereof, are effectively useful as medicines and agricultural chemicals. Processes are also disclosed for preparing such compounds.Type: GrantFiled: July 11, 1990Date of Patent: October 5, 1993Assignee: Nippon Chemiphar Co., Ltd.Inventors: Mitsuo Masaki, Haruhiko Shinozaki, Masaru Satoh, Naoya Moritoh, Koichi Hashimoto, Toshiro Kamishiro
-
Patent number: 5232980Abstract: There are provided N-substituted carbonyloxyalkylpyrrole compounds of formula I ##STR1## and their use for the control of insects, acarina and mollusks. Further provided are compositions and methods comprising those compounds for the protection of plants from attack by insects, acarina and mollusks.Type: GrantFiled: October 27, 1992Date of Patent: August 3, 1993Assignee: American Cyanamid CompanyInventors: David G. Kuhn, Stephen F. Donovan, Joseph A. Furch
-
Patent number: 5233052Abstract: This invention relates to new diarylpyrrolecarbonitrile and new diarylnitropyrrole compounds. It also relates to the use of said compounds as insecticidal and acaricidal agents and to a method of protecting plants, particularly crop plants, from attack by insects and acarina by application of a new diarylpyrrolecarbonitrile or diarylnitropyrrole to said plants or to the locus in which they are growing.Type: GrantFiled: September 24, 1992Date of Patent: August 3, 1993Assignee: American Cyanamid CompanyInventors: David G. Kuhn, Joseph A. Furch, Victor M. Kamhi
-
Patent number: 5229393Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.Type: GrantFiled: April 6, 1992Date of Patent: July 20, 1993Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey
-
Patent number: 5229524Abstract: Bis- and tris(trifluoromethyl)arylpyrrole compounds which are effective for the control of insects and acarids are described. A method for the insecticidal and acaricidal use of said compounds and methods for the preparation of said compounds are presented.Type: GrantFiled: October 13, 1992Date of Patent: July 20, 1993Assignee: American Cyanamid CompanyInventors: Venkataraman Kameswaran, Victor M. Kamhi
-
Patent number: 5223530Abstract: Novel arylcycloalkanepolyalkylamines useful as anti-psychotic, anti-ischemia, anti-stroke, anti-dementia and anti-convulsant agents. These arylcycloalkanepolyalkylamines are selective high-affinity ligands to the sigma binding-sites containing three basic units: arylcycloalkyl group, an amine group and an intermediate chain. Their preparation and use for treatment of psychoses, ischemia, stroke, dementia and convulsions are also disclosed.Type: GrantFiled: September 12, 1991Date of Patent: June 29, 1993Assignee: SRI, InternationalInventor: Daniel W. Parish
-
Patent number: 5196532Abstract: Compounds of formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or methyl, A is an ethylene or methylene radical which is unsubstituted or substituted by methyl, hydroxyl or oxo,L is a saturated or unsaturated five-membered or six-membered heterocyclic structure which is unsubstituted or substituted by hydroxyl, mercapto, C.sub.1 -C.sub.6 -alkyl, or C.sub.1 -C.sub.4 -alkanoyl and has from 1 to 3 heteroatoms from the group consisting of N, O and S, the second and third heteroatoms being a nitrogen atom,R.sup.3 is hydrogen, a hydroxy or C.sub.1 -C.sub.6 -alkoxy group,R.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen or methoxy,R.sup.5 is hydrogen or methoxy or tert-butyl,R.sup.6 is hydrogen methyl, nitrile or a C.sub.2 -C.sub.10 -ketal group or the radical --CHR.sup.7 OR.sup.8 --CHR.sup.7 --NR.sup.9 R.sup.10, --COR.sup.11, --SR.sup.12, ##STR2## in which R.sup.7 is hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sup.8 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.Type: GrantFiled: June 18, 1991Date of Patent: March 23, 1993Assignee: BASF AktiengesellschaftInventors: Hans-Heiner Wuest, Bernd Janssen, William V. Murray, Michael P. Wachter, Stanley Bell
-
Patent number: 5166216Abstract: Methyl .alpha.-arylacrylates substituted by a heterocyclic radical and having the general formula ##STR1## where R is alkyl, alkenyl, haloalkyl, cycloalkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, halogen or aryl, the aromatic ring being unsubstituted or substituted, Het is a five-membered heteroaromatic ring which is unsubstituted or substituted and has from one to three heteroatoms, and A is ethenylene, ethylene, methyleneoxy or methylenethio, and fungicides and pesticides containing these compounds.Type: GrantFiled: May 13, 1991Date of Patent: November 24, 1992Assignee: BASF AktiengesellschaftInventors: Franz Schuetz, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Ulrich Schirmer, Peter Hofmeister, Christoph Kuenast, Eberhard Ammermann, Gisela Lorenz, Uwe Kardorff
-
Patent number: 5164409Abstract: All possible stereoisomers and mixtures of a compound of the formula ##STR1## wherein X and Y are different and are selected from the group consisting of hydrogen, halogen, --CN, alkyl and haloalkyl of 1 to 8 carbon atoms and phenyl optionally substituted by at least one member of the group consisting of halogen and alkyl and alkoxy of 1 to 8 carbon atoms, R.sub.1 is selected from the group consisting of hydrogen, methyl, --CN and ethynyl, ##STR2## A and B are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 8 carbon atoms and aryl of 6 to 14 carbon atoms and the --CF.sub.3 is in the 2-, 4- or 5-position of the pyrrole ring having pesticidal activity.Type: GrantFiled: February 26, 1991Date of Patent: November 17, 1992Assignee: Roussel UclafInventors: Marc Benoit, Jacques Demassey, Jean-Pierre Demoute, Jean Tessier
-
Patent number: 5151536Abstract: There is provided a single step procedure for the manufacture of 1-(alkoxymethyl)pyrrole compounds by reacting the appropriate pyrrole precursor with a dihalomethane reagent in the presence of an alkali metal alkoxide. The 1-(alkoxymethyl)pyrrole compounds are useful as molluscicidal, insecticidal, acaricidal and nematocidal agents.Type: GrantFiled: December 17, 1990Date of Patent: September 29, 1992Assignee: American Cyanamid CompanyInventors: Venkataraman Kameswaran, Jerry M. Barton
-
Patent number: 5128485Abstract: There is provided a synthesis of 2-aryl-5-(trifluoromethyl)pyrrole compounds via the condensation of a suitable enamine with an .alpha.-haloketone.Type: GrantFiled: December 17, 1990Date of Patent: July 7, 1992Assignee: American Cyanamid CompanyInventor: Venkataraman Kameswaran
-
Patent number: 5118685Abstract: Aminopropanol derivatives of the formula: ##STR1## where R.sup.1 and R.sup.2 are identical or different and are each hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl or hydroxyalkyl, each of not more than 6 carbon atoms, alkoxyalkyl, alkylthioalkyl or dialkylaminoalkyl, each of not more than 9 carbon atoms in total, or phenylalkyl or phenoxyalkyl where the alkyl radical is of not more than 6 carbon atoms and the phenyl radical is unsubstituted or substituted by alkyl or alkoxy, each of not more than 3 carbon atoms, or R.sup.1 and R.sup.2, together with the nitrogen atom which links them, form a 5-membered to 7-membered saturated heterocyclic ring which can be substituted by one or two phenyl and/or hydroxyl radicals and can contain an oxygen or nitrogen atom, as a further heteroatom in the ring, and such an additional nitrogen atom can be substituted by alkyl of 1 to 3 carbon atoms or by phenyl, and -- .circle.Type: GrantFiled: December 3, 1984Date of Patent: June 2, 1992Assignee: BASF AktiengesellschaftInventors: Albrecht Franke, Wolfgang Spiegler, Hardo Siegel, Claus D. Mueller, Gerda von Philipsborn, Dieter Lenke, Josef Gries
-
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
-
Patent number: 5106985Abstract: There is provided a process for the preparation of 4-substituted-5-(trifluoromethyl)pyrrole-3-carbonitrile compounds which are useful as insecticidal, nematicidal and acaricidal agents.Type: GrantFiled: November 16, 1990Date of Patent: April 21, 1992Assignee: American Cyanamid CompanyInventor: Venkataraman Kameswaran
-
Patent number: 5057504Abstract: Pesticidal bicyclo-octanes are of the formula ##STR1## where R is a substituted or unsubstituted aliphatic or aromatic group, R' and R.sup.3 are H or a substituted or unsubstituted aliphatic or aromatic group, R.sup.2 is a substituted or unsubstituted heterocyclic group containing at least one ring nitrogen and is preferably a 3- or 4- pyridyl group, Z is CH.sub.2 CH.sub.2, CH.sub.2 O--CH.sub.2 S or COCH.sub.2 or CH(OR.sup.5)CH.sub.2 where R.sup.5 is H, alkyl, acyl or carbamoyl at Y and Y' are O or S(O).sub.m where m is 0, 1 or 2.Various methods for their preparation are described.Type: GrantFiled: August 16, 1989Date of Patent: October 15, 1991Assignee: The Wellcome Foundation LimitedInventors: Malcolm H. Black, John A. Wyatt, John B. Weston, John P. Larkin, Ian H. Smith, David A. Pulman
-
Patent number: 5055484Abstract: 7-[1H-pyrrol-3-yl]-substituted 3,5-dihydroxyhept-6-enoic acids, 7-[1H-pyrrol-3-yl]-substituted 3,5-dihydroxyheptanoic acids of the formula I ##STR1## in which A, B, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the indicated meanings, and the corresponding .delta.-lactones of the formula II ##STR2## processes for the preparation of these compounds, their use as medicaments and pharmaceutical products are described. In addition, new intermediates for the preparation of the compounds of the formulae I and II are described.Type: GrantFiled: July 8, 1988Date of Patent: October 8, 1991Assignee: Hoechst AktiengesellschaftInventors: Heiner Jendralla, Gerhard Beck, Ekkehard Baader, Bela Kerekjarto
-
Patent number: 5043349Abstract: Substituted pyrroles, pyrazoles and triazoles such as ##STR1## and their pharmaceutically suitable salts are useful as antihypertensive agents and for treatment of congestive heart failure.Type: GrantFiled: March 26, 1990Date of Patent: August 27, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Carini, David J., John J. V. Duncia, Gregory J. Wells
-
Patent number: 5041442Abstract: This invention is directed to compounds of formula (I): ##STR1## wherein R.sup.1 is thiocyano, --CH.sub.2 CN, --NH.sub.2, --NHR.sup.5, or --CH.sub.2 OR.sup.5 where R.sup.5 is lower alkyl;R.sup.2 is hydrogen, halo, lower alkyl, or lower alkylthio;R.sup.3 is hydrogen, halo, lower alkyl, lower alkylthio, or thiocyano;R.sup.4 is hydrogen, halo, lower alkyl, lower alkoxy, lower alkylthio, or lower alkylsulfonyl; andY is --O--CH.sub.2 --, --S--CH.sub.2 --, --CH.dbd.CH--, or --(CH.sub.2).sub.n -- where n is 0, 1, 2, 3 or 4;or a pharmaceutically acceptable salt thereof. These compounds are useful in treating mammals having disease-states characterized by excessive gastric acid secretion.Type: GrantFiled: July 31, 1990Date of Patent: August 20, 1991Assignee: Syntex (U.S.A.) Inc.Inventors: Ruth S. Romero, Fidencio Franco, Armando C. Castaneda, Joseph M. Muchowski
-
Patent number: 5034409Abstract: Heterocyclic acids and esters useful as inhibitors of mammalian blood platelet aggregation characterized by Formula I are disclosed.HET.sub.1 --(CH.sub.2).sub.n CO.sub.2 R (I)Formula I compounds are those wherein n is 6-9, R is hydrogen, lower alkyl or an alkali metal ion, and HET.sub.1 is the heterocyclic radical 3,4-diphenyl-1H-pyrrol-1-yl.Type: GrantFiled: February 13, 1990Date of Patent: July 23, 1991Assignee: Bristol-Myers Squibb CompanyInventor: Nicholas A. Meanwell
-
Patent number: 5010189Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonization of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: October 24, 1989Date of Patent: April 23, 1991Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst
-
Patent number: 4999429Abstract: Aryl difluoromethyl sulfone adds to aldehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.Type: GrantFiled: November 13, 1989Date of Patent: March 12, 1991Assignee: Ethyl CorporationInventor: G. Patrick Stahly
-
Patent number: 4997848Abstract: Compounds of formula (I): ##STR1## in which: R represents hydrogen, methyl of hydroxy; X represents an alkyl, alkenyl, cycloalkyl, aryl, aralkyl, or heterocyclic group; A represents a single bond, or an alkylene, alkenylene, alkynylene or alkadienylene group; Y represents hydrogen, or an aryl, cycloalkyl or heterocyclic group] have valuable antihypercholesteremic activities and may be used in the treatment of disorders arising from a blood cholesterol imbalance in humans and other animals.Type: GrantFiled: October 21, 1988Date of Patent: March 5, 1991Assignee: Sankyo Company, LimitedInventors: Masaaki Kurabayashi, Hiroshi Kogen, Hiroshi Kadokawa, Hideshi Kurihara, Kazuo Hasegawa, Masao Kuroda
-
Patent number: 4992462Abstract: For inhibiting 3-hydroxy-3-methyl-glutaryl coenzyme A (HMG-CoA) reductase, the novel substituted pyrroles of the formula ##STR1## in which R.sup.1 is optionally alkyl or cycloalkyl,R.sup.2 and R.sup.3 each is optionally substituted aryl or heteroaryl,R.sup.4 is H or an organic radical,X is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--,A is ##STR2## R.sup.7 is H or alkyl, and R.sup.8 is H or an ester or cation radical.Novel intermediates therefor are also provided.Type: GrantFiled: April 7, 1988Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt, Gunter Thomas
-
Patent number: 4980361Abstract: Abstract of the disclosure: p-hydroxy phenone derivatives of the formula I ##STR1## where X is ##STR2## where R.sup.1 =F, Cl, Br or trifluoromethyl or a heteroaryl of the structure ##STR3## with R.sup.2 =C.sub.1 -C.sub.4 -alkyl, Y is a bridging member of the formula --CH.dbd.CH--, --CH.sub.2 CH.sub.2 -- or --CH.sub.2 --,is one of the numbers 2, 3 or 4 andis an amino group of the formula --NR.sup.2 R.sup.3 or N-pyrrolidyl or N-piperidyl, where R.sup.2 and R.sup.3 are, independently of one another, C.sub.1 -C.sub.4 -alkyl, as well as the physiologically tolerated salts thereof, are used for preparing antiarrhythmic drugs.Type: GrantFiled: July 13, 1989Date of Patent: December 25, 1990Assignee: BASF AktiengesellschaftInventors: Wilfried Lubisch, Gerda von Philipsborn
-
Patent number: 4973704Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1-6 alkyl not containing an asymmetric carbon atom, C.sub.3-7 cycloalkyl or ##STR2## wherein R.sub.5, R.sub.6 and R.sub.7 are as defined below, R.sub.2 is C.sub.1-6 alkyl not containing an asymmetric carbon atom, C.sub.3-7 cycloalkyl or ##STR3## wherein R.sub.8, R.sub.9 and R.sub.10 are as defined below, R.sub.3 is hydrogen, C.sub.1-6 alkyl not containing an asymmetric carbon atom, C.sub.3-7 cycloalkyl or ##STR4## wherein R.sub.11, R.sub.12 and R.sub.13 are as defined below, R.sub.4 is hydrogen, C.sub.1-6 alkyl not containing an asymmetric carbon atom, C.sub.3-7 cycloalkyl or ##STR5## wherein R.sub.14, R.sub.15 and R.sub.16 are as defined below, X is --(CH.sub.2).sub.m --, --CH.dbd.CH--, --CH.dbd.CH--CH.sub.2 --or --CH.sub.2 --CH.dbd.CH--, wherein m is 0, 1, 2 or 3, andZ is ##STR6## wherein R.sub.17 is hydrogen or C.sub.1-3 alkyl, andR.sub.18 is hydrogen, R.sub.19 or M,whereinR.sub.Type: GrantFiled: April 14, 1989Date of Patent: November 27, 1990Assignee: Sandoz Pharm. Corp.Inventor: James R. Wareing
-
Patent number: 4973696Abstract: A stereoselective process is described for preparing optically active alpha,beta-disubstituted carbonyl compounds, comprising forming an acetal between an alpha,beta-unsaturated aldehyde or ketone and tartaric acid or a derivative thereof, halogenating the product thus obtained, and restoring the carbonyl compound.Type: GrantFiled: January 17, 1989Date of Patent: November 27, 1990Assignee: Zambon S.p.A.Inventors: Claudio Giordano, Graziano Castaldi, Silvia Cavicchioli, Francesco Minisci
-
Patent number: 4940707Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are lower-alkyl; or together are alkylene with 3-5 C-atoms in a straight chain; one of the residues R.sup.3 and R.sup.4 is hydrogen and the other is hydrogen or lower-alkyl; R.sup.6 and R.sup.7 are hydrogen or lower-alkyl; R.sup.5 and R.sup.8 are hydrogen, lower-alkyl, lower-alkoxy or halogen; X signifies --O--, --S--, --SO--, --SO.sub.2 -- or --NR.sup.9 ; R.sup.9 is hydrogen, lower-alkyl or acyl; Y is --S(O).sub.m R.sup.10 or --NHet and, where X is --NR.sup.9 --, --S--, --SO-- or --SO.sub.2 --, also --N(R.sup.11).sub.2 or --OR.sup.12 ; R.sup.10 is lower-alkyl; R.sup.11 and R.sup.12 are hydrogen, lower-alkyl or acyl; --NHet is a 5-8 membered, saturated or unsaturated, monocyclic heterocycle, attached via a N-atom; n is 2, 3 or 4 and m is 0, 1 or 2, are described. The compounds of formula I are useful as agents for the treatment of disorders such as neoplasms, dermatoses or ageing of the skin.Type: GrantFiled: February 14, 1989Date of Patent: July 10, 1990Assignee: Hoffman-La Roche Inc.Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
-
Patent number: 4929751Abstract: A vinyl tricarbonyl compound of the formula ##STR1## or its monohydrate of the formula ##STR2## wherein R.sub.1 is a hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, and cycloalkyl with 3 to 7 carbon atoms,R.sub.2 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic,R.sub.3 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic, andR.sub.4 is unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl are 3 to 7 carbon atoms. Such vinyl tricarbonyl compound is effective against tumor cells.Type: GrantFiled: October 19, 1987Date of Patent: May 29, 1990Assignee: Yale UniversityInventors: Harry H. Wasserman, Natesan Murugesan, John H. Van Duzer
-
Patent number: 4913721Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.Type: GrantFiled: October 31, 1988Date of Patent: April 3, 1990Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey
-
Patent number: 4904679Abstract: Pyrrolophenylalkanolamines of the formula ##STR1## R.sup.1 and R.sup.2 represent hydrogen or various radicals, R.sup.3 represents hydrogen, acyl or trialkylsilyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 represents hydrogen, or, together with R.sup.3, represents ##STR2## wherein R.sup.7 represents hydrogen or alkyl, andR.sup.6 represents branched or cyfclic alkyl, which is optionally substituted,and salts thereof promote the yield of animals. Many new intermediates are also shown.Type: GrantFiled: April 22, 1988Date of Patent: February 27, 1990Assignee: Bayer AktiengesellschaftInventors: Hartmund Wollweber, Jurgen Stoltefuss, Friedrich Berschauer, Ann de Jong, Martin Scheer
-
Patent number: 4900839Abstract: A series of novel heterocyclic-substituted 2-(1H)-quinolone compounds have been prepared, including the 3,4-dihydro derivatives thereof, wherein the heterocyclic ring moiety is a pyrrolyl, imidazolyl, pyrazolyl, triazolyl or tetrazolyl group attached by a nitrogen atom of said group to the 5-, 6-, 7- or 8-positions of the quinolone ring. These particular compounds are useful in therapy as highly potent inotropic agents and therefore, are of value in the treatment of various cardiac conditions. Preferred member compounds include 6-(2,4-dimethylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, 6-(2,4-dimethyl-5-nitroimidazol-1-yl)-8-methyl-2-(1H)-quinolone, 8-methyl-6-(tetrazol-1-yl)-2-(1H)-quinolone, 8-methyl-6-(1,2,4-triazol-4-yl)-2-(1H)-quinolone, and 6-(4-cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, respectively. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: January 27, 1989Date of Patent: February 13, 1990Assignee: Pfizer Inc.Inventors: Simon F. Campbell, David A. Roberts
-
Patent number: 4897397Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.Type: GrantFiled: December 16, 1988Date of Patent: January 30, 1990Assignee: Schering CorporationInventors: Neng Y. Shih, David J. Blythin