Chalcogen Attached Indirectly To The Five-membered Hetero Ring By Acyclic Nonionic Bonding Patents (Class 548/562)
  • Patent number: 5367084
    Abstract: 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: Grant
    Filed: October 26, 1993
    Date of Patent: November 22, 1994
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: John Verkade, Jiansheng Tang
  • Patent number: 5359090
    Abstract: 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: Grant
    Filed: December 29, 1993
    Date of Patent: October 25, 1994
    Assignee: American Cyanamid Company
    Inventors: Robert F. Doehner, Jerry M. Barton
  • Patent number: 5354862
    Abstract: 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: Grant
    Filed: August 31, 1993
    Date of Patent: October 11, 1994
    Assignee: Rohm and Haas Company
    Inventor: Adam C. Hsu
  • Patent number: 5352820
    Abstract: 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: Grant
    Filed: June 28, 1993
    Date of Patent: October 4, 1994
    Inventor: Jeremy I. Levin
  • Patent number: 5340835
    Abstract: 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: Grant
    Filed: January 19, 1993
    Date of Patent: August 23, 1994
    Assignee: Roussel-UCLAF
    Inventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute, Fabienne Pilorge, Nicole Reinier
  • Patent number: 5330981
    Abstract: 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: Grant
    Filed: December 30, 1992
    Date of Patent: July 19, 1994
    Assignee: Istituto Gentili S.p.A.
    Inventors: Sergio Rosini, Maurizio Mian
  • Patent number: 5326911
    Abstract: 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: Grant
    Filed: July 20, 1992
    Date of Patent: July 5, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz-Ulrich Blank, Helmut Kraus, Gerhard Marzolph, Nikolaus Muller
  • Patent number: 5310938
    Abstract: 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: Grant
    Filed: July 13, 1993
    Date of Patent: May 10, 1994
    Assignee: American Cyanamid Company
    Inventors: Dale G. Brown, Robert E. Diehl, Donald P. Wright, Jr., Jack K. Siddens, deceased
  • Patent number: 5300508
    Abstract: 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: Grant
    Filed: January 31, 1992
    Date of Patent: April 5, 1994
    Assignee: Centre National de la Recherche Scientifique
    Inventors: Alain Valla, Michel Giraud, Marc Bazin, Rene Santus
  • Patent number: 5286743
    Abstract: 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: Grant
    Filed: October 27, 1992
    Date of Patent: February 15, 1994
    Assignee: American Cyanamid Company
    Inventors: David G. Kuhn, Stephen F. Donovan, Joseph A. Furch
  • Patent number: 5286741
    Abstract: 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: Grant
    Filed: October 27, 1992
    Date of Patent: February 15, 1994
    Assignee: American Cyanamid Company
    Inventors: David G. Kuhn, Stephen F. Donovan, Joseph A. Furch
  • Patent number: 5281719
    Abstract: 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: Grant
    Filed: April 23, 1993
    Date of Patent: January 25, 1994
    Assignee: American Cyanamid Company
    Inventors: Venkataraman Kameswaran, Victor M. Kamhi
  • Patent number: 5278184
    Abstract: 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: Grant
    Filed: April 17, 1992
    Date of Patent: January 11, 1994
    Assignee: Repla Chemical Ltd.
    Inventors: Marino Artico, Federico Corelli, Silvio Massa, Antonello Mai, Enzo Tramontano
  • Patent number: 5278295
    Abstract: 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: Grant
    Filed: May 7, 1992
    Date of Patent: January 11, 1994
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Hirofumi Suzuki, Takehira Kaneko, Nobuo Matsui, Isami Hamamoto, Tetsuya Katoh, Toshiaki Satoh, Fuminiko Nagasaki
  • Patent number: 5258382
    Abstract: 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: Grant
    Filed: June 19, 1992
    Date of Patent: November 2, 1993
    Assignee: Dainippon Pharmaceutical Co., Ltd.
    Inventors: Toshiyuki Negoro, Makoto Murata, Shozo Ueda, Buichi Fujitani, Yoshiyuki Ono
  • Patent number: 5256796
    Abstract: 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: Grant
    Filed: December 11, 1992
    Date of Patent: October 26, 1993
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 5254713
    Abstract: 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: Grant
    Filed: February 10, 1993
    Date of Patent: October 19, 1993
    Assignee: Nihon Bayer Agrochem K.K.
    Inventors: Shinzo Kagabu, Itsumi Kawai, Katsuaki Wada
  • Patent number: 5254559
    Abstract: 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: Grant
    Filed: December 4, 1991
    Date of Patent: October 19, 1993
    Assignee: American Cyanamid Company
    Inventors: David G. Kuhn, Venkataraman Kameswaran
  • Patent number: 5250546
    Abstract: 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: Grant
    Filed: July 11, 1990
    Date of Patent: October 5, 1993
    Assignee: Nippon Chemiphar Co., Ltd.
    Inventors: Mitsuo Masaki, Haruhiko Shinozaki, Masaru Satoh, Naoya Moritoh, Koichi Hashimoto, Toshiro Kamishiro
  • Patent number: 5232980
    Abstract: 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: Grant
    Filed: October 27, 1992
    Date of Patent: August 3, 1993
    Assignee: American Cyanamid Company
    Inventors: David G. Kuhn, Stephen F. Donovan, Joseph A. Furch
  • Patent number: 5233052
    Abstract: 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: Grant
    Filed: September 24, 1992
    Date of Patent: August 3, 1993
    Assignee: American Cyanamid Company
    Inventors: David G. Kuhn, Joseph A. Furch, Victor M. Kamhi
  • Patent number: 5229393
    Abstract: 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: Grant
    Filed: April 6, 1992
    Date of Patent: July 20, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey
  • Patent number: 5229524
    Abstract: 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: Grant
    Filed: October 13, 1992
    Date of Patent: July 20, 1993
    Assignee: American Cyanamid Company
    Inventors: Venkataraman Kameswaran, Victor M. Kamhi
  • Patent number: 5223530
    Abstract: 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: Grant
    Filed: September 12, 1991
    Date of Patent: June 29, 1993
    Assignee: SRI, International
    Inventor: Daniel W. Parish
  • Patent number: 5196532
    Abstract: 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: Grant
    Filed: June 18, 1991
    Date of Patent: March 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Heiner Wuest, Bernd Janssen, William V. Murray, Michael P. Wachter, Stanley Bell
  • Patent number: 5166216
    Abstract: 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: Grant
    Filed: May 13, 1991
    Date of Patent: November 24, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Schuetz, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Ulrich Schirmer, Peter Hofmeister, Christoph Kuenast, Eberhard Ammermann, Gisela Lorenz, Uwe Kardorff
  • Patent number: 5164409
    Abstract: 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: Grant
    Filed: February 26, 1991
    Date of Patent: November 17, 1992
    Assignee: Roussel Uclaf
    Inventors: Marc Benoit, Jacques Demassey, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 5151536
    Abstract: 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: Grant
    Filed: December 17, 1990
    Date of Patent: September 29, 1992
    Assignee: American Cyanamid Company
    Inventors: Venkataraman Kameswaran, Jerry M. Barton
  • Patent number: 5128485
    Abstract: There is provided a synthesis of 2-aryl-5-(trifluoromethyl)pyrrole compounds via the condensation of a suitable enamine with an .alpha.-haloketone.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: July 7, 1992
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 5118685
    Abstract: 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: Grant
    Filed: December 3, 1984
    Date of Patent: June 2, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Albrecht Franke, Wolfgang Spiegler, Hardo Siegel, Claus D. Mueller, Gerda von Philipsborn, Dieter Lenke, Josef Gries
  • Patent number: 5118704
    Abstract: 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: Grant
    Filed: September 11, 1991
    Date of Patent: June 2, 1992
    Assignee: Whitby Research, Inc.
    Inventors: Gevork Minaskanian, James V. Peck
  • Patent number: 5106985
    Abstract: 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: Grant
    Filed: November 16, 1990
    Date of Patent: April 21, 1992
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 5057504
    Abstract: 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: Grant
    Filed: August 16, 1989
    Date of Patent: October 15, 1991
    Assignee: The Wellcome Foundation Limited
    Inventors: Malcolm H. Black, John A. Wyatt, John B. Weston, John P. Larkin, Ian H. Smith, David A. Pulman
  • Patent number: 5055484
    Abstract: 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: Grant
    Filed: July 8, 1988
    Date of Patent: October 8, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heiner Jendralla, Gerhard Beck, Ekkehard Baader, Bela Kerekjarto
  • Patent number: 5043349
    Abstract: 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: Grant
    Filed: March 26, 1990
    Date of Patent: August 27, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Carini, David J., John J. V. Duncia, Gregory J. Wells
  • Patent number: 5041442
    Abstract: 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: Grant
    Filed: July 31, 1990
    Date of Patent: August 20, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Ruth S. Romero, Fidencio Franco, Armando C. Castaneda, Joseph M. Muchowski
  • Patent number: 5034409
    Abstract: 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: Grant
    Filed: February 13, 1990
    Date of Patent: July 23, 1991
    Assignee: Bristol-Myers Squibb Company
    Inventor: Nicholas A. Meanwell
  • Patent number: 5010189
    Abstract: 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: Grant
    Filed: October 24, 1989
    Date of Patent: April 23, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4999429
    Abstract: 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: Grant
    Filed: November 13, 1989
    Date of Patent: March 12, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4997848
    Abstract: 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: Grant
    Filed: October 21, 1988
    Date of Patent: March 5, 1991
    Assignee: Sankyo Company, Limited
    Inventors: Masaaki Kurabayashi, Hiroshi Kogen, Hiroshi Kadokawa, Hideshi Kurihara, Kazuo Hasegawa, Masao Kuroda
  • Patent number: 4992462
    Abstract: 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: Grant
    Filed: April 7, 1988
    Date of Patent: February 12, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt, Gunter Thomas
  • Patent number: 4980361
    Abstract: 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: Grant
    Filed: July 13, 1989
    Date of Patent: December 25, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wilfried Lubisch, Gerda von Philipsborn
  • Patent number: 4973704
    Abstract: 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: Grant
    Filed: April 14, 1989
    Date of Patent: November 27, 1990
    Assignee: Sandoz Pharm. Corp.
    Inventor: James R. Wareing
  • Patent number: 4973696
    Abstract: 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: Grant
    Filed: January 17, 1989
    Date of Patent: November 27, 1990
    Assignee: Zambon S.p.A.
    Inventors: Claudio Giordano, Graziano Castaldi, Silvia Cavicchioli, Francesco Minisci
  • Patent number: 4940707
    Abstract: 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: Grant
    Filed: February 14, 1989
    Date of Patent: July 10, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
  • Patent number: 4929751
    Abstract: 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: Grant
    Filed: October 19, 1987
    Date of Patent: May 29, 1990
    Assignee: Yale University
    Inventors: Harry H. Wasserman, Natesan Murugesan, John H. Van Duzer
  • Patent number: 4913721
    Abstract: 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: Grant
    Filed: October 31, 1988
    Date of Patent: April 3, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey
  • Patent number: 4904679
    Abstract: 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: Grant
    Filed: April 22, 1988
    Date of Patent: February 27, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmund Wollweber, Jurgen Stoltefuss, Friedrich Berschauer, Ann de Jong, Martin Scheer
  • Patent number: 4900839
    Abstract: 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: Grant
    Filed: January 27, 1989
    Date of Patent: February 13, 1990
    Assignee: Pfizer Inc.
    Inventors: Simon F. Campbell, David A. Roberts
  • Patent number: 4897397
    Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: January 30, 1990
    Assignee: Schering Corporation
    Inventors: Neng Y. Shih, David J. Blythin