Nitrogen Attached Indirectly To The Five-membered Hetero Ring By Acyclic Nonionic Bonding Patents (Class 548/561)
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Patent number: 5391772Abstract: Described is a process for converting an alcohol to an azide with S.sub.N 2 inversion using a phosphoryl azide, e.g. diphenylphosphoryl azide (DPPA). Good yields of azide in high enantiomeric excess can be achieved specifically for benzylic alcohols and alpha-hydroxy alkyl esters. The process is carried at preferably room temperature in an inert dry aprotic solvent, e.g. toluene, and in the presence of a proton acceptor, e.g. 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to afford high yields of high enantiomeric purities.Type: GrantFiled: July 8, 1993Date of Patent: February 21, 1995Assignee: Merck & Co., Inc.Inventors: Andrew S. Thompson, Edward J. J. Grabowski
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Patent number: 5389616Abstract: The compounds of the formula ##STR1## wherein A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as set forth above, are described.The compounds of formula I have an inhibitory activity on the natural enzyme renin and can accordingly be used in the form of pharmaceutical preparations for the control or prevention of high blood pressure and cardiac insufficiency.Type: GrantFiled: July 29, 1993Date of Patent: February 14, 1995Assignee: Hoffman-LaRoche Inc.Inventors: Quirico Branca, Werner Neidhart, Jenri Ramuz, Henri Ramuz, Heinz Stadler, Wolfgang Wostl
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Patent number: 5378839Abstract: 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: January 26, 1994Date of Patent: January 3, 1995Assignee: American Cyanamid CompanyInventors: David G. Kuhn, Venkataraman Kameswaran
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Patent number: 5371239Abstract: 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 nitropyrrole or pyrrole carbonitrile compound.Type: GrantFiled: February 26, 1992Date of Patent: December 6, 1994Assignee: American Cyanamid CompanyInventor: Mary E. Doscher
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Patent number: 5371076Abstract: The invention provides compounds of the formula: ##STR1## wherein R, R.sup.1, R.sup.2 and W are defined in the specification. These compounds are useful as antibiotic agents.Type: GrantFiled: April 2, 1993Date of Patent: December 6, 1994Assignee: American Cyanamid CompanyInventors: Ving J. Lee, Brian L. Buckwalter, Timothy C. Barden
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Patent number: 5364844Abstract: Compounds of formula (I): ##STR1## A is a carbon-carbon bond or C.sub.1 -C.sub.3 alkylene; B is imino group or C.sub.1 -C.sub.2 alkylene; R.sup.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, heterocyclic or optionally substituted amino; R.sup.2 is optionally substituted phenyl or optionally substituted naphthyl; R.sup.3 is thiazolyl, isoxazolyl or imidazolyl; R.sup.4 is isopropyl or cyclohexyl; R.sup.5 and R.sup.6 are C.sub.1 -C.sub.4 alkyl, or, together with the carbon atom to which they are attached, C.sub.3 -C.sub.7 cycloalkyl; R.sup.7 is hydrogen, optionally substituted C.sub.1 -C.sub.6 alkyl group; and R.sup.8 is hydrogen or C.sub.1 -C.sub.4 alkyl. These compounds have renin-inhibitory and, hence, hypotensive activities. The invention also provides a method for the treatment or prophylaxis of hypertension induced by failures in the renin-angiotensin system.Type: GrantFiled: August 27, 1992Date of Patent: November 15, 1994Assignee: Sankyo Company, LimitedInventors: Yasuhiro Morisawa, Mitsuru Kataoka, Yuichiro Yabe, Hiroyuki Koike, Yasuteru Iijima, Hidekuni Takahagi, Tatsuo Kokubu, Kunio Hiwada
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Patent number: 5362746Abstract: There are provided novel intermediates useful in preparing insecticidal 2-aryl-4-halopyrrole compounds, a novel insecticidal compound, 4-chloro-1-(ethoxymethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3- carbonitrile, and compositions and methods of use thereof.Type: GrantFiled: November 23, 1992Date of Patent: November 8, 1994Assignee: American Cyanamid CompanyInventors: Venkataraman Kameswaran, Robert Francis
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Patent number: 5362885Abstract: Disclosed herein are N-substituted-3-(nitrogen-containing 5-membered ring)benzenesulfonamide derivatives of the formula (I): ##STR1## R.sup.1 is H, Cl, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.4 alkoxycarbonyl; Z is CH or N; X.sup.1 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxyl or Cl; and X.sup.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxyl, a process for the preparation thereof, and herbicidal compositions containing the N-substituted-3-(nitrogen-containing 5-membered ring)benzenesulfonamide derivatives as active ingredients.Type: GrantFiled: June 25, 1993Date of Patent: November 8, 1994Assignee: Kureha Kagaku Kogyo K.K.Inventors: Hideo Arabori, Shiro Yamazaki, Masato Arahira, Aiko Murakami
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Patent number: 5359089Abstract: There is provided a process for the preparation of 2,4,5-tribromopyrrole-3-carbonitrile. 2,4,5-Tribromo -pyrrole-3-carbonitrile is useful as a molluscicidal agent.Type: GrantFiled: December 22, 1993Date of Patent: October 25, 1994Assignee: American Cyanamid CompanyInventor: Victor M. Kamhi
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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
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Patent number: 5350871Abstract: The invention relates to a method of preparing an optically active cyanohydrin by addition of hydrogen cyanide to a carbonyl compound, selected from aldehydes and ketones, in the presence of hydroxynitrile lyase, in a biphasic solvent system, comprising a homogeneous aqueous solution of said enzyme, and a suitable organic solvent which is at least substantially immiscible with water. Said method is performed in that said homogeneous aqueous solution is buffered with an acetate buffer having a buffer concentration of between 0.005 and 0.1 mole per liter or with a non-acetate buffer, that the volume ratio organic phase:aqueous phase is between approx. 5:1 and approx. 1:5, and that a solution of hydrogen cyanide and said carbonyl compound in said organic solvent is properly mixed during the reaction period with said homogeneous aqueous solution of hydroxynitrile lyase.Type: GrantFiled: December 8, 1992Date of Patent: September 27, 1994Assignee: Duphar International Research B.V.Inventors: Hendrik W. Geluk, Wybrand T. Loos
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Patent number: 5349063Abstract: A novel group of radiolabelled diamines are provided, effective for pancreatic imaging and represented by the formula ##STR1## wherein n is 1 to 10; R.sub.1 and R.sub.2 are the same or different and are hydrogen, hydroxyl or lower alkyl having 1 to 6 carbon atoms; R.sub.3 is lower alkyl having 1 to 6 carbon atoms; and N' is a nitrogen atom forming part of a 4- to 8-membered heterocyclic ring containing one or two hetero atoms, one of which is said nitrogen, said heterocyclic ring being unsubstituted or substituted with one or more lower alkyl groups and pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: January 4, 1993Date of Patent: September 20, 1994Assignee: Alberta Cancer BoardInventors: Alummoottil V. Joshua, John R. Scott
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Patent number: 5344836Abstract: A fused benzenoxyacetic acid derivative of the formula (I): ##STR1## and salts thereof possess an agonistic on PGI.sub.2 receptor, so it is useful for prevention and/or treatment of thrombosis, arteriosclerosis, ischemic heart diseases, gastric ulcer and hypertention.Type: GrantFiled: November 5, 1992Date of Patent: September 6, 1994Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Nobuyuki Hamanaka, Kanji Takahashi, Hidekado Tokumoto
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Patent number: 5336783Abstract: A novel calpain inhibitory active and low molecular weight substance, cystamidin A and its production are provided. Cystamidin A of the following formula ##STR1## was produced by culturing Streptomyces sp. KP-1241 FERM BP-41 71 in a nutrient medium and isolating the active substance from the cultured mass.Type: GrantFiled: March 23, 1993Date of Patent: August 9, 1994Assignee: The Kitasato InstituteInventors: Satoshi Omura, Haruo Tanaka, Kazuro Shiomi, Jing R. Liu
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Patent number: 5328909Abstract: A novel cyclopropenone derivative (I) which possesses a potent inhibitory activity against thiol protease such as papain, cathepsin B, cathepsin H, cathepsin L, calpain or the like with excellent properties regarding oral absorbance, tissue transference and cell membrane permeability, and are clinically useful in the treatment of various diseases such as muscular dystrophy, amyotrophy. Also provided are a process for producing the compound (I) and a pharmaceutical composition containing the same.Type: GrantFiled: June 25, 1992Date of Patent: July 12, 1994Assignee: Mitsubishi Kasei CorporationInventors: Ryoichi Ando, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
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Patent number: 5326883Abstract: The present invention provides certain substituted oxime ether compounds which inhibit lipoxygenase enzyme activity and are useful in the treatment of allergic and inflammatory disease states. The compounds of this invention have the structure ##STR1## where M is hydrogen, a pharmaceutically acceptable cation, or a pharmaceutically acceptable metabolically cleavable group; p and q are independently zero or one, with the provisos that (i) p and q may not both be the same; (ii) when p is one and q is zero, R is selected from the group consisting of hydrogen, straight or branched alkyl of from one to twelve carbon atoms, and cycloalkyl of from three to eight carbon atoms; and (iii) when p is zero and q is one, R is selected from the group consisting of hydrogen, alkyl of from one to twelve carbon atoms, cycloalkyl of from three to eight carbon atoms, and --NR.sub.1 R.sub.2.L.sub.Type: GrantFiled: December 18, 1992Date of Patent: July 5, 1994Assignee: Abbott LaboratoriesInventors: Dee W. Brooks, Andrew O. Stewart, Robert G. Maki
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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
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Patent number: 5310918Abstract: Disclosed is a non-linear optical material represented by the following formula: ##STR1## wherein X represents a methyl group or a hydrogen atom, with the proviso that when X is a methyl group, A represents a nitrogen atom, Y represents a methyl group and B represents a nitrogen atom; and when X is a hydrogen atom , A represents C--COOC.sub.2 H.sub.5, Y represents a hydrogen atom and B represents C--CH.sub.3.In one embodiment, the non-linear optical material is represented by the following formula (I): ##STR2## In another embodiment, the non-linear optical material is represented by the following formula (II): ##STR3## Also disclosed is an orthorhomic molecular crystal having a space group of Pna2.sub.1 and constituted by molecules represented by the above formula (I).Type: GrantFiled: May 15, 1991Date of Patent: May 10, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Nobuhiko Uchino, Masaki Okazaki, Makoto Ishihara, Akinori Harada, Yoji Okazaki, Kazumi Kubo
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Patent number: 5304604Abstract: Compounds of general formula I: ##STR1## wherein: R.sup.1 represents a hydrogen atom or a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, phenyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkylthiomethyl, phenylthiomethyl, substituted phenylthiomethyl, phenyl(C.sub.1 -C.sub.6)alkylthiomethyl or heterocyclylthiomethyl group; or R.sup.1 represents --SR.sup.x wherein R.sup.x represents a group ##STR2## R.sup.2 represents a hydrogen atom or a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, phenyl(C.sub.1 -C.sub.6)alkyl, cycloalkyl(C.sub.1 -C.sub.6)alkyl, or cycloalkenyl(C.sub.1 -C.sub.6)alkyl;R.sup.3 represents an amino acid residue with R or S stereochemistry or a C.sub.1 -C.sub.6 alkyl, benzyl, (C.sub.1 -C.sub.6)alkoxybenzyl or benzyloxy(C.sub.1 -C.sub.6)alkyl group;R.sup.4 represents a hydrogen atom or a methyl group;n is an integer from 1 to 6; andA represents the group --NH.sub.Type: GrantFiled: April 15, 1991Date of Patent: April 19, 1994Assignee: British Bio-technology LimitedInventors: Alan H. Davidson, Jonathan P. Dickens, Michael J. Crimmin
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Patent number: 5302724Abstract: This invention provides certain sulfonamide compounds, formulations and method of use of certain sulfonamide compounds in treating susceptible neoplasms.Type: GrantFiled: April 29, 1992Date of Patent: April 12, 1994Assignee: Eli Lilly and CompanyInventors: J. Jeffry Howbert, Fariborz Mohamadi, Michael M. Spees
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Patent number: 5302370Abstract: The invention relates to compounds having the general formula I ##STR1## where A if required can contain a functional and/or activated group C for coupling to selectively concentrating compounds or can contain a selectively concentrating compound coupled via the group C. B and B' are functional groups for coordinate bonding of groups carrying metal ions. The novel compounds are for forming complexes with radioactive metal ions, more particularly rhenium and technetium isotopes, and are used in medical diagnosis and therapy.Type: GrantFiled: August 22, 1990Date of Patent: April 12, 1994Assignee: Institut fur Diagnostikforschung GmbHInventors: Reinhard Neumeier, Wolfgang Kramp, Helmut R. Macke
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Patent number: 5292732Abstract: The novel pyrrolopyrazines of the general formula ##STR1## wherein one of R.sup.1 and R.sup.2 signifies aryl and the other signifies hydrogen, lower alkyl or aryl or R.sup.1 and R.sup.2 together with the two carbon atoms denoted by .alpha. and .beta. signify the group A; ##STR2## R.sup.3 signifies hydrogen or lower alkyl and R.sup.4 signifies hydrogen orR.sup.3 and R.sup.4 together signify an additional C/N bond;R.sup.5 signifies hydrogen or lower alkyl;R.sup.6 signifies hydrogen or lower alkyl;R.sup.7 signifies hydrogen, halogen, lower alkyl, optionally substituted lower alkoxy, or C.sub.3-6 -cycloalkyl, C.sub.4-6 -cycloalkenyl, C.sub.Type: GrantFiled: June 26, 1992Date of Patent: March 8, 1994Assignee: Hoffmann-La Roche Inc.Inventor: Stephan Rover
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Patent number: 5292760Abstract: Novel 4,5-dihydro-4-heteroaryl-3H-1,3-benzodiazepines, intermediates, processes for the preparation thereof, and methods for treating depression, inhibiting convulsions and treating anxiety utilizing compounds and compositions thereof are disclosed.Type: GrantFiled: April 22, 1992Date of Patent: March 8, 1994Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Joseph F. Payack, Salvatore M. Brucato
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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
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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
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Patent number: 5281625Abstract: Guanidines I ##STR1## (A=C.sub.5 -C.sub.12 -cycloalkyl which may bear up to three further substituents; benzyl substituted in the para-position; R.sup.1, R.sup.2, R.sup.3 =H, C.sub.1 -C.sub.4 -alkyl; R.sup.4 =C.sub.5 -C.sub.18 -alkyl which may be interrupted by oxygen, C.sub.5 -C.sub.18 -alkenyl, C.sub.4 -C.sub.18 -alkynyl or phenyl-C.sub.1 -C.sub.6 -alkyl, and these groups may bear up to three further substituents and the phenyl moiety of the phenylalkyl may additionally bear a phenoxy group or up to three C.sub.2 -C.sub.4 -alkenyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.6 -alkyl or haloalkyl groups, C.sub.5 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.8 -alkyl, where the ring may bear up to three further substituents; A=benzyl and R.sup.4 =C.sub.3 -C.sub.4 -alkyl which may be interrupted by oxygen, or C.sub.4 -alkenyl, both of which may bear up to three further substituents; R.sup.3 +R.sup.4 =C.sub.5 -C.sub.Type: GrantFiled: December 4, 1991Date of Patent: January 25, 1994Assignee: BASF AktiengesellschaftInventors: Matthias Zipplies, Hubert Sauter, Franz Roehl, Eberhard Ammermann, Gisela Lorenz
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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
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Patent number: 5276147Abstract: The subject of the present invention is compounds which correspond to the following general formula: ##STR1## in which R.sub.1 and R.sub.3 independently of one another represent H, an alkyl, alkenyl, cycloalkyl, aryl, arylalkyl or an alkylaryl group, a heterocycle, or groups which are unsubstituted or substituted, in particular by one or more hydroxyl or alkoxy groups or halogen;n represents an integer from 1 to 5;i in each case takes values from 1 to n for the n successive ##STR2## links; R.sub.2, R.sub.4.sup.i and R.sub.5.sup.i independently of one another represent H, an alkyl, alkenyl, aryl, alkoxy, hydroxyalkyl, alkoxyalkyl, amido, acyl or carboxyalkyl group, or a salt, or an alkyl ester of the latter; or R.sub.4.sup.i and R.sub.5.sup.i together form an oxo group ##STR3## R.sub.6 and R.sub.7 represent H, or R.sub.6 and R.sub.7 together form an oxo group ##STR4## x represents a 5- or 6-membered heterocycle which contains at least one nitrogen atom, or, in the event that ##STR5## where R.sub.8 and R.sub.Type: GrantFiled: April 19, 1990Date of Patent: January 4, 1994Assignee: Medgenix Group S.A.Inventors: John R. Thornback, Marcel Deblaton, Gillian F. Morgan
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Patent number: 5268488Abstract: Disclosed are an acrylate series compound represented by the following formula: ##STR1## wherein R.sup.1 represents a C.sub.1-10 alkoxy group, a halogen atom, a C.sub.1-6 alkyl group, a nitro group, a C.sub.1-6 alkylamino group, a C.sub.1-6 alkylthio group, a halo C.sub.1-6 alkyl group, a pyrrole group, a C.sub.1-6 alkylsulfonyl group, a cyano group, a C.sub.1-6 mono- or dialkylaminosulfonyl group, a phenoxy group which may have a C.sub.1-6 alkoxy group, a benzyloxy group, a halo C.sub.1-6 alkoxy group, a C.sub.3-6 alkenyloxy group, a hydroxyl group, a C.sub.2-7 cyanoalkoxy group, a C.sub.3-6 alkynyloxy group, a C.sub.1-6 alkoxy group substituted by a C.sub.3-6 cycloalkyl group, a C.sub.1-6 alkoxy group substituted by a C.sub.1-6 alkoxy group, a C.sub.2-7 alkoxycarbonyl group or a C.sub.2-7 acyl; R.sup.2 represents a C.sub.3-8 cycloalkyl group which may have a C.sub.1-6 alkyl group; n represents an integer of 0 to 5; a plural number of R.sup.1 s may be the same or different; and when n is 2, two R.sup.Type: GrantFiled: September 11, 1992Date of Patent: December 7, 1993Assignee: Ube Industries, Ltd.Inventors: Masanori Watanabe, Toshinobu Tanaka, Hisato Kobayashi, Shuji Yokoyama, Hideaki Umeyama
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Patent number: 5258526Abstract: A process for the preparation of 3-substituted 4-cyanopyrrole compounds of the formula (I) ##STR1## in which Ar has the meaning given in the description, by reaction in a 1st stage of bromides (II)Ar--Br (II)with acrylonitrile in the presence of a solvent and a suitable reaction auxiliary to give acrylonitrile derivatives (III)Ar--CH.dbd.CH--CN (III)and in a 2nd stage with a phenylsulphonylmethyl isocyanide (IV)Ph--SO.sub.2 --CH.sub.2 --CN (IV)in the presence of a solvent and optionally in the presence of a suitable reaction auxiliary, characterised in that the 1st stage is carried out in the presence of a palladium catalyst and the 2nd stage in the presence of a 1.2- to 1.8-fold molar excess of alkali metal alcoholate or alkali metal hydroxide.Type: GrantFiled: February 28, 1992Date of Patent: November 2, 1993Assignee: Bayer AktiengesellschaftInventors: Peter C. Knuppel, Reinhard Lantzsch, Klaus Jelich, Peter Andres, Albrecht Marhold
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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
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Patent number: 5256645Abstract: The compounds of the formula ##STR1## wherein A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as set forth above, are described.The compounds of formula I have an inhibitory activity on the natural enzyme renin and can accordingly be used in the form of pharmaceutical preparations for the control or prevention of high blood pressure and cardiac insufficiency.Type: GrantFiled: April 22, 1992Date of Patent: October 26, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Quirico Branca, Werner Neidhart, Henri Ramuz, Heinz Stadler, Wolfgang Wostl
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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
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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
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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
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Patent number: 5246946Abstract: A piperidine compound has the generic formula and is useful to treat arrhythmia. ##STR1## in which R1 is a lower alkyl and W is: ##STR2## X is --S--, --SO-- or --SO2--, R2 is hydrogen or --(CH2)n--Y, n is an integer of 1 to 5, Y is an aryl, pyridyl or a substituted pyridyl, X' is --CO-- or --CH(OH)--,p is an integer of 1 to 4, R12 is hydrogen or a lower alkyl, Y' is --(CH2)m--A, m is 1 or 2, A is an aryl, a substituted aryl, pyridyl or a substituted pyridyl, R12 and Y may form a 5- or 6-membered ring or a 5- or 6-membered ring having one or more substituents andR22 is hydrogen, a halogen, a lower alkyl, a lower alkoxy or hydroxy.Type: GrantFiled: August 14, 1992Date of Patent: September 21, 1993Assignee: Eisai Co., Ltd.Inventors: Hitoshi Oinuma, Motosuke Yamanaka, Kazutoshi Miyake, Tomonori Hoshiko, Norio Minami, Tadao Shoji, Yoshiharu Daiku, Kohei Sawada, Kenichi Nomoto
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Patent number: 5245040Abstract: A process for the preparation of 1,3-disubstituted 2-nitroguanidines of the formula I ##STR1## in which R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or a radical --CH.sub.2 B; A is an unsubstituted or mono- to tetrasubstituted aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical, which may contain one or two substituents from the group comprising C.sub.1 -C.sub.3 haloalkyl having 1 to 7 halogen atoms, cyclopropyl, halocyclopropyl having 1 to 3 halogen atoms, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.2 -C.sub.3 haloalkenyl and C.sub.2 -C.sub.3 haloalkynyl having 1 to 4 halogen atoms, C.sub.1 -C.sub.3 haloalkoxy having 1 to 7 halogen atoms, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio having 1 to 7 halogen atoms, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro and one to four substituents from the group comprising C.sub.1 -C.sub.3 alkyl, C.sub.Type: GrantFiled: October 16, 1991Date of Patent: September 14, 1993Assignee: Ciba-Geigy CorporationInventors: Peter Maienfisch, Odd Kristiansen, Laurenz Gsell
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Patent number: 5245034Abstract: Novel quinoline sulfonamino derivatives having a vessel smooth muscle relaxation activity as well as a platelet agglutination inhibitory activity and inhibitory activity to protein kinase A, myosin light chain kinase, proteinkinase C, and calmodulindependent proteinkinase II, but having little action or cardio function; a process for the production of the derivatives, and a pharmaceutical composition containing the derivative.Type: GrantFiled: March 23, 1992Date of Patent: September 14, 1993Assignee: Kiroyoshi HidakaInventors: Hiroyoshi Hidaka, Tomohiko Ishikawa, Masatoshi Hagiwara, Tsutomu Inoue, Kenji Naitoh, Osamu Sakuma, Masayuki Yuasa, Tadashi Morita, Tadashi Toshioka, Isao Umezawa, Takashi Inaba
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Patent number: 5234943Abstract: Fungicidally active 3-(2-chloro-3-trifluoro-methylphenyl)-4-cyanopyrrole of the formula ##STR1##Type: GrantFiled: August 17, 1992Date of Patent: August 10, 1993Assignee: Bayer AktiengesellschaftInventors: Ulrich Heinemann, Albrecht Marhold, Stefan Dutzmann, Heinz-Wilhelm Dehne
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Patent number: 5234946Abstract: The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7,X and Y are linking groups,R.sup.2 is H or lower alkyl,R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl,R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms,R.sup.Type: GrantFiled: August 30, 1991Date of Patent: August 10, 1993Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Hiroshi Takezawa, Masahiro Hayashi, Yoshikazu Iwasawa, Masaaki Hosoi, Yoshiaki Iida, Yoshimi Tsuchiya, Masahiro Horie, Toshio Kamei
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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
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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
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Patent number: 5229404Abstract: Novel O-alkylated oximes of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 are optionally substituted aromatic or heteroaromatic rings, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is a nitrogen containing, substituted ring or an amino group carrying a substituted ring, and n and m independently are 0, 1 or 2, are potent inhibitors of GABA re-uptake from the synaptic cleft.Type: GrantFiled: December 6, 1991Date of Patent: July 20, 1993Assignee: Novo Nordisk A/SInventors: Lars J. S. Knutsen, Knud E. Andersen, Anker S. Jorgensen, Ursula Sonnewald
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Patent number: 5227401Abstract: Compounds characterized generally as ethynyl alanine amino diol derivatives are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are those of Formula I ##STR1## wherein A is selected from CO and SO.sub.2 wherein X is selected from oxygen atom and methylene; wherein each of R.sub.1 and R.sub.9 is a group independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, benzyl, .beta.,.beta.,.beta.-trifluoroethyl, t-butyloxycarbonyl and methoxymethylcarbonyl, and wherein the nitrogen atom to which R.sub.1 and R.sub.9 are attached may be combined with oxygen to form an N-oxide; wherein R.sub.2 is selected from hydrido, methyl, ethyl and isopropyl; wherein R.sub.3 is selected from benzyl, cyclohexylmethyl, phenethyl, imidazolemethyl, pyridylmethyl and 2-pyridylethyl; wherein R.sub.5 is propargyl or a propargyl-containing moiety; wherein R.sub.7 is cyclohexylmethyl; wherein each of R.sub.4 and R.sub.6 is independently selected from hydrido and methyl; wherein R.Type: GrantFiled: October 29, 1991Date of Patent: July 13, 1993Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran
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Patent number: 5223535Abstract: Compounds characterized generally as propargyl glycine amino propargyl diol derivatives are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are those of Formula I ##STR1## wherein A is selected from CO and SO.sub.2 wherein X is selected from oxygen atom and methylene; wherein each of R.sub.1 and R.sub.9 is a group independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, benzyl, .beta.,.beta.,.beta.-trifluoroethyl, t-butyloxycarbonyl and methoxymethylcarbonyl, and wherein the nitrogen atom to which R.sub.1 and R.sub.9 are attached may be combined with oxygen to form an N-oxide; wherein R.sub.2 is selected from hydrido, methyl, ethyl and isopropyl; wherein R.sub.3 is selected from benzyl, cyclohexylmethyl, phenethyl, imidazolemethyl, pyridylmethyl and 2-pyridylethyl; wherein each of R.sub.5 and R.sub.8 is independently propargyl or a propargyl-containing moiety; wherein R.sub.7 is cyclohexylmethyl; wherein each of R.sub.4 and R.sub.Type: GrantFiled: October 29, 1991Date of Patent: June 29, 1993Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran
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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
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Patent number: 5216150Abstract: Novel quinoline sulfonamino derivatives having a vessel smooth muscle relaxation activity as well as a platelet agglutination inhibitory activity and inhibitory activity to protein kinase A, myosin light chain kinase, proteinkinase C, and calmodulindependent proteinkinase II, but having little action or cardio function; a process for the production of the derivatives, and a pharmaceutical composition containing the derivative.Type: GrantFiled: September 12, 1991Date of Patent: June 1, 1993Assignees: Hiroyoshi Hidaka, Tobishi Yakuhin Kogyo Kabushiki KaishaInventors: Hiroyoshi Hidaka, Tomohiko Ishikawa, Masatoshi Hagiwara, Tsutomu Inoue, Kenji Naitoh, Osamu Sakuma, Masayuki Yuasa, Tadashi Morita, Tadashi Toshioka, Isao Umezawa, Takashi Inaba
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Patent number: 5207816Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1 is alkyl, R.sup.2 is alkyl, unsubstituted or halogen-substituted alkenyl or alkynyl, X is a substituted or unsubstituted five-membered heteroaromatic radical, and Z is hydrogen, methoxycarbonyl, ethoxycarbonyl, methyl or cyano, processes for their manufacture, and the use of these compounds for controlling undesirable plant growth.Type: GrantFiled: June 6, 1991Date of Patent: May 4, 1993Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Dieter Jahn, Michael Keil, Hans Theobald, Wolfgang Spiegler, Bruno Wuerzer
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Patent number: 5204332Abstract: There are provided certain insecticidal, acaricidal and molluscicidal pyrrole carbonitrile and nitropyrrole compounds and a method for controlling insects, acarids and mollusks therewith. The invention also provides a method for protecting growing plants from insect, acarid and mollusk attack by applying to said plants or the soil or water in which they are growing, an insecticidally, acaricidally or molluscicidally effective amount of a pyrrole carbonitrile or nitropyrrole compound. The present invention further relates to methods for the preparation of said pyrrole carbonitrile and nitropyrrole compounds.Type: GrantFiled: November 20, 1991Date of Patent: April 20, 1993Assignee: American Cyanamid CompanyInventors: Dale G. Brown, Robert E. Diehl, Gregory T. Lowen, Donald P. Wright, Jr., Christine F. Kukel, Rod A. Herman, Roger W. Addor
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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