Phthalazines (including Hydrogenated) Patents (Class 544/237)
  • Patent number: 4863948
    Abstract: A series of novel alkanesulphonamidophenyl-N-alkyl-N-(heterocyclic-alkyl)alkylamine derivatives have been prepared, including their pharmaceutically acceptable salts, wherein the heterocyclic moiety is a 5- or 6-membered nitrogen-containing heterocyclic group which is attached to the adjacent carbon atom by a carbon or nitrogen atom and optionally contains a further heteroatom selected from oxygen and nitrogen, said nitrogen-containing heterocyclic group being either (i) substituted by a phenyl or benzyl group or (ii) fused at two adjacent carbon atoms to a benzene ring, with the resulting heterocyclic ring moiety also being optionally substituted. These particular compounds are useful in therapy as highly effective anti-arrhythmic agents and therefore, are of value in the treatment of various cardiac arrythmias. The most preferred member compound of the series is 2-hydroxy-2-(4-methanesulphonamidophenyl)-N-methyl-N-[2-(6-chloro-2H-isoin dolin-1-on-2-yl)ethyl]ethylamine.
    Type: Grant
    Filed: April 9, 1987
    Date of Patent: September 5, 1989
    Assignee: Pfizer, Inc.
    Inventors: John E. Arrowsmith, Peter E. Cross, Geoffrey N. Thomas
  • Patent number: 4863945
    Abstract: Pyrrolobenzimidazoles of the formula: ##STR1## are useful for treatment of heart and circulatory diseases. R.sub.1 is substituted phenyl; or optionally substituted naphthyl or a five- or six-membered heterocyclic group which can be condensed with a phenyl ring to form a bicyclic radical. R.sub.2 is hydrogen, alkyl, alkenyl or cycloalkenyl; R.sub.3 is alkyl, alkenyl or hydroxyalkyl or with R.sub.2 together forms cycloakylene; or R.sub.2 and R.sub.3 together form alkylidene or cycloalkylidene. R.sub.4 is hydrogen or lower alkanoyl. X is a valency bond, alkylene, vinylene, imino or carbonylamino. T stands for two hydrogen atoms. When X is a valency bond, R.sub.1 can also be hydrogen, hydrocarbyl which may also contain oxygen, amino, sulfur, carbonyl and sulfonyl groups. When X is imino or carbonylamino or when R.sub.1 is a bicyclic radical, T can also be oxygen. The compounds also include the tautomers and physiologically acceptable salts with inorganic and organic acids.
    Type: Grant
    Filed: December 10, 1987
    Date of Patent: September 5, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Walter-Gunar Friebe, Alfred Mertens, Klaus Strein, Erwin Boehm
  • Patent number: 4861564
    Abstract: The compounds of the invention comprise the condensation product, as well as derivatives thereof, of two equivalents of a trimethyl cyclohexane-anhydride acid chloride derivative with one equivalent of an aromatic diamine. The scope of the invention includes the method of using the compounds of the invention as chelating agents for metals, metal ions or ions of metal complexes. In a preferred embodiment of the invention the binding moieties of the cyclohexane derivatives are rigidly held opposite each other, by restricting their rotation about the N-C aryl bonds, in order to more effectively bind the metals or the ions.
    Type: Grant
    Filed: October 2, 1987
    Date of Patent: August 29, 1989
    Assignee: Year Laboratories, Inc.
    Inventor: Julius Rebek
  • Patent number: 4847251
    Abstract: The present invention provides pyridazinone derivatives of the general formula: ##STR1## wherein Het is a mono- or bicyclic heterocycle with one or two nitrogen atoms, B-C is a --CHR.sub.1 --CH.sub.2 --, --CR.sub.1 .dbd.CH--, --CHR.sub.1 --O--, --O--CHR.sub.1 --, --CHR.sub.1 --NH-- or --NH--CHR.sub.1 -- group, R.sub.1 being a hydrogen atom or an alkyl radical, and A is an amiono, alkylcarbonylamino, aminocarbonylamino, aminothiocarbonylamino, alkylaminothiocarbonylamino, alkylamionocarbonylamino, N'-cyanoguanidino or N'-cyano-N"-alkylguanidino group, a substituted phenyl ring or heterocycle attached via a nitrogen or sulphur atom, or a mono- or bicyclic substituted heterocycle with 1 to 3 nitrogen atoms, one ring nitrogen atom being directly attached to Het; as well as the physiologically acceptable salts thereof.The present invention also provides processes for the preparation of these pyridazinone drivatives and pharmaceutical compositions containing them for the treatment of heart and circulatory diseases.
    Type: Grant
    Filed: August 3, 1987
    Date of Patent: July 11, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Wolfgang Von Der Saal, Bernd Muller-Beckmann, Gisbert Sponer
  • Patent number: 4841047
    Abstract: There are provided 4-benzyl-1-(2H)-phthalazinone derivatives having antiallergic activity of the formula ##STR1## wherein R.sub.1 represents fluorine, chlorine, bromine, trifluoromethyl, C.sub.1 -C.sub.6 -alkyl, hydroxy, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkanoyloxy, amino, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.6 -alkanoylamino, C.sub.2 -C.sub.6 -alkanoyl-C.sub.1 -C.sub.6 -alkylamino or a nitro group, R.sub.2 represents hydrogen or has one of the meanings given for R.sub.1, whereby R.sub.1 and R.sub.2 may be the same or different, the radicals R.sub.3 and R.sub.4 are the same or different and represent hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, hydroxy, C.sub.1 -C.sub.6 -alkoxy, benzyloxy or C.sub.2 -C.sub.6 -alkanoyloxy and A represents an azacycloalkanyl radical, the aza nitrogen of which contains a C.sub.1 -C.sub.6 -alkyl group which is substituted by various radicals, and processes for their manufacture.
    Type: Grant
    Filed: November 10, 1986
    Date of Patent: June 20, 1989
    Assignee: Aasta Pharma AG
    Inventors: Jurgen Engel, Gerhard Scheffler
  • Patent number: 4835268
    Abstract: Disclosed herein are derivatives of 5-(lower alkyl)-7-amino-2,3-dihydro-1,4-phthalazinedione having substituents on the amino group. The derivatives have luminescent properties which render them useful as analytical tools in clinical chemistry. Adaptation of the derivatives for luminescent immunoassay provides valuable reagents and assays with outstanding sensitivity.
    Type: Grant
    Filed: May 7, 1987
    Date of Patent: May 30, 1989
    Assignee: Universite Laval
    Inventors: Alain Belanger, Paul Brassard
  • Patent number: 4831031
    Abstract: Arylpiperazinyl-ethyl(or butyl)-heterocyclic compounds and their pharmaceutically acceptable acid addition salts are neuroleptic agents. They are useful in the treatment of psychotic disorders.
    Type: Grant
    Filed: January 22, 1988
    Date of Patent: May 16, 1989
    Assignee: Pfizer Inc.
    Inventors: John A. Lowe, III, Arthur A. Nagel
  • Patent number: 4824846
    Abstract: Compounds I ##STR1## where A equals CH or N; Ar equals naphthyl, thienyl or phenyl; R.sup.1 equals alkyl, F or Cl; g equals zero, 1 or 2; and Y equals various heterocyclic bases, and the acid-addition salts thereof, are described.Several preparation processes are described.The compounds IIIa ##STR2## where R.sup.1, g and Y are as specified in the case of the formula I, serve as intermediates for the preparation of these compounds. Processes are also specified for the preparation of IIIa.I represent valuable antimycotics.
    Type: Grant
    Filed: March 19, 1987
    Date of Patent: April 25, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus D. Kampe, Wolfgang Raether, Walter Dittmar, Heinz Hanel
  • Patent number: 4822878
    Abstract: Novel chromophor derivatives of cyclic anhydrides are provided which have the ability to react with a variety of organic substrates forming adducts which are useful in analytical techniques for the detection and measurement of biological compounds.
    Type: Grant
    Filed: May 27, 1988
    Date of Patent: April 18, 1989
    Assignee: Viomedics, Inc.
    Inventor: Spyros Theodoropulos
  • Patent number: 4820842
    Abstract: The present invention provides a process for preparing a 5-cyano-2-substituted-1,4-dihydropyridine compound having cardiovascular activity.
    Type: Grant
    Filed: September 11, 1987
    Date of Patent: April 11, 1989
    Assignee: Warner-Lambert Company
    Inventors: Kevin R. Anderson, Ila Sircar
  • Patent number: 4806535
    Abstract: This invention relates to imidazolylphenyl and 1,2,4-triazolylphenyl benzopyridazinone and pyridopyridazinone compounds of the formula ##STR1## wherein A is CH or N and not more than one of W, X, Y and Z is a N atom which possess valuable pharmaceutical preparations, e.g., increasing cardiotonic contractility. Uses of said compounds including methods for increasing cardiac contractility and in the treatment of congestive heart failure, pharmaceutical compositions including the same and methods for the preparation thereof.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: February 21, 1989
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: William C. Faith, Henry F. Campbell, Donald E. Kuhla, William L. Studt, James L. Barnes
  • Patent number: 4789742
    Abstract: Novel Isomaleimido and isophthalimido derivatives of chromophoric compounds are provided which are useful in analytic techniques for the detection and measurement of biological compounds such as bacteria, enzymes, hormones and the like.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: December 6, 1988
    Inventor: Spyros Theodoropulos
  • Patent number: 4785101
    Abstract: Benzodiazinone-pyridazinone and -hydroxypyrazolyl compounds possess cardiotonic activity and are included in therapeutic cardiotonic compositions useful in methods for increasing cardiac contractility and for the treatment of congestive heart failure.
    Type: Grant
    Filed: June 17, 1987
    Date of Patent: November 15, 1988
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: Donald E. Kuhla, Henry F. Campbell, William L. Studt, William C. Faith, Bruce F. Molino
  • Patent number: 4772747
    Abstract: Disclosed is a process for the preparation of 2,4,6-trichlorophenylhydrazine by chlorinating the reaction product of phenylhydrazine and a dicarboxylic anhydride to obtain an N-(2,4,6-trichloroanilino)dicarboximide which is reacted with a base capable of liberating 2,4,6-trichlorophenylhydrazine therefrom.
    Type: Grant
    Filed: October 28, 1983
    Date of Patent: September 20, 1988
    Assignee: Eastman Kodak Company
    Inventors: Kevin J. Edgar, John A. Hyatt
  • Patent number: 4769369
    Abstract: Novel 1 2(H)-phthalazones are disclosed along with a method of treating either allergic rihinitis or bronchial asthma by the administration to a mammal an effective amount of a compound of the formula: ##STR1## wherein R.sub.1 is hydrogen, hydroxyl, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio,R.sub.2 is ##STR2## or 1-pyrrolidinyl, R.sub.3 and R.sub.4 are independently hydrogen or C.sub.1 -C.sub.4 alkyl,X is CH.sub.2, O or NR.sub.5,Y is ethylene or ethenylene,R.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl,n is 2, 3 or 4,and all stereoisomeric forms and pharmaceutical acceptable addition salts thereof.
    Type: Grant
    Filed: November 14, 1986
    Date of Patent: September 6, 1988
    Assignee: Pennwalt Corporation
    Inventors: Telfer L. Thomas, Lesley A. Radov
  • Patent number: 4743541
    Abstract: A luminescent substrate preparation having a concentration of catalytic inhibitors of less than about 100 ppm. The preparation is obtained by heating commercial grade luminol in a basic solution, crystallizing the luminol and separating the luminol crystals from the boiled solution. The heating, crystallization and separation steps are preferably repeated sequentially at least four times, with the starting material for each sequence after the first being the luminol preparation produced in the previous sequence. The luminol preparation has an enhanced pattern of activity, in that light output is substantially constant over a period of at least about one hour, with the intensity of light emitted by the preparation being at least about ten times that of commercially available luminol. Because of these enhanced characteristics, the luminol preparation is particularly adapted for use as a tag in specific binding assays where the concentration of analyte to be detected is low.
    Type: Grant
    Filed: July 17, 1985
    Date of Patent: May 10, 1988
    Assignee: Mast Immunosystems, Inc.
    Inventors: Keith W. Higgins, Christopher R. Brown, John F. Burd
  • Patent number: 4740320
    Abstract: Novel compositions are prepared by reacting hydrocarbyl substituted nitrogen-containing aromatic heterocyclic compounds such as 2,5-dimethylpyridine or 2,4,6-collidine, an aldehyde such as formaldehyde, or a ketone such as acetone, or mixtures thereof and an amine having a combined total of at least seven carbon, nitrogen, oxygen or sulfur atoms and at least one reactive amine hydrogen atom such as 1-dodecanamine in the presence of a suitable catalyst such as hydrogen chloride. These novel compositions, as well as their free amine forms are useful as oil and gas well corrosion inhibitors.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: April 26, 1988
    Assignee: The Dow Chemical Company
    Inventors: Duane S. Treybig, Robert G. Martinez
  • Patent number: 4731370
    Abstract: This invention relates to a novel 1,4-dihydropyridine derivative of the formula ##STR1## wherein R2 is pyridyl, or a salt thereof. These compounds have a vasodilating activity and a platelet aggregation inhibiting activity. Also disclosed are pharmaceutical compositions containing the same.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: March 15, 1988
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Isao Watanabe, Kaishu Momonoi, Toru Hiraiwa, Satoshi Ono, Joji Nakano, Katsuyuki Nagumo, Hiroyasu Takagi
  • Patent number: 4710499
    Abstract: The present invention relates to derivatives of pyridazine of formula: ##STR1## in which R.sub.1 is alkyl or a phenyl group and R.sub.2 is H or R.sub.1 and R.sub.2 form, with the carbon atoms to which they are attached, a benzene cycle, R.sub.3 is H or phenyl and R.sub.4 is ##STR2## in which R.sub.5 is H or CH.sub.3 and R.sub.6 is H, OH, OR or OCOR; it also relates to a process for preparing the products of formula (I) and to the drugs containing at least one of said products.
    Type: Grant
    Filed: August 7, 1984
    Date of Patent: December 1, 1987
    Assignee: Sanofi
    Inventors: Camille G. Wermuth, Jean-Pierre Chambon
  • Patent number: 4707479
    Abstract: 1,4-Dihyropyridinecarboxamides of the formula ##STR1## and salts thereof, are effective for treating cardiac insufficiency, thromboses, thromboembolisms and ischaemias, for influencing the blood-sugar level and the circulation and as coronary therapeutic agents and anti-arrhythmic agents.
    Type: Grant
    Filed: December 5, 1985
    Date of Patent: November 17, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Meyer, Gerhard Franckowiak, Ulrich Rosentreter, Rainer Gross, Gunter Thomas, Matthias Schramm, Michael Kayser, Friedel Seuter, Elisabeth Perzborn, Martin Bechem
  • Patent number: 4698425
    Abstract: The compounds of the invention comprise the condensation product, as well as derivatives thereof, of two equivalents of a trimethyl cyclohexane-anhydride acid chloride derivative with one equivalent of an aromatic diamine. The scope of the invention includes the method of using the compounds of the invention as chelating agents for metals, metal ions or ions of metal complexes. In a preferred embodiment of the invention the binding moieties of the cyclohexane derivatives are rigidly held opposite each other, by restricting their rotation about the N-C aryl bonds, in order to more effectively bind the metals or the ions.
    Type: Grant
    Filed: July 24, 1984
    Date of Patent: October 6, 1987
    Assignee: Year Laboratories, Inc.
    Inventor: Julius Rebek
  • Patent number: 4698352
    Abstract: This invention relates to a novel 4-oxo-1,4-dihydronicotinic acid derivative ##STR1## or a salt thereof, wherein R.sup.1 is hydrogen or carboxyl-protecting group;R.sup.2 is substituted phenyl and naphthyl, or a substituted or unsubstituted heterocyclic group; andR.sup.3 is haloalkyl, aminoalkyl, or substituted or unsubstituted alkenyl, phenylalkenyl, naphthylalkenyl, phenylalkyl, naphthylalkyl, phenylalkynyl, naphthylalkynyl, heterocyclic alkyl, heterocyclic alkenyl, phenyl, naphthyl, cycloalkyl, cycloalkenyl, carboxylic acyl, iminoalkyl, heterocyclic or bridged hydrocarbon, which has a broad antibacterial spectrum and a low toxicity, and are useful for treatment of diseases of human beings and animals, to a process for producing the same and to an antibacterial agent containing the same.
    Type: Grant
    Filed: October 27, 1983
    Date of Patent: October 6, 1987
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Hirokazu Narita, Yoshinori Konishi, Jun Nitta, Shunjiro Misumi, Hideyoshi Nagaki, Isao Kitayama, Yoriko Nagai, Yasuo Watanabe, Nobuyuki Matsubara, Shinzaburo Minami, Isamu Saikawa
  • Patent number: 4668677
    Abstract: Certain new 1-alkylamino-4-phenylphthalazine derivatives, 1-neopentylamino-4-phenylphthalazine and 1-(1-ethylpropylamino)-4-phenylphthalazine, having prominent activity to ameliorate circulatory disorders and prepared from the corresponding phthalazinones.
    Type: Grant
    Filed: April 11, 1985
    Date of Patent: May 26, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Yasuhiro Morinaka, Katsuhiko Iseki, Toshiji Kanayama, Toshiaki Watanabe, Hiroyoshi Nishi
  • Patent number: 4665181
    Abstract: A compound useful as anti-inflammatory agents in warm-blooded animals of the formula ##STR1## wherein X is a member of the class of ethylene and ethenyl and is substituted for hydrogen in the sixth or seventh position of the 1(2H)-phthalazinone ringY is a member of the class of hydrogen and hydroxylR.sub.1 is a member of the class of hydrogen, alkyl, alkoxy, hydroxyl, halogen, nitro, --NR.sub.3 R.sub.4, --COR.sub.5 and --O--A wherein A is a mineral acid residue which with --O-- forms an ester or the alkali metal salt of said ester,R.sub.2 is a member of the class of hydrogen, alkyl, phenyl, substituted phenyl, heteroaryl, hydroxyalkylene, polyhydroxyalkylene, aminoalkylene, alkylaminoalkylene, and carboxyalkylene,R.sub.3, R.sub.4 are independently from the class of hydrogen, alkyl, aminoalkylene or alkylaminoalkylene,R.sub.5 is a member of the class of OR.sub.
    Type: Grant
    Filed: May 17, 1984
    Date of Patent: May 12, 1987
    Assignee: Pennwalt Corporation
    Inventors: Telfer L. Thomas, Lesley A. Radov
  • Patent number: 4661484
    Abstract: There are provided novel pyridazinone derivatives having the general formula (I): ##STR1## wherein A represents 5- or 6-membered heterocyclic ring having 1-3 nitrogen atoms, which may be substituted by at least one member selected from the group consisting of C.sub.1-5 alkyl, cyano, hydroxyl, C.sub.1-5 alkoxy, amino, C.sub.1-5 alkylamino, C.sub.2-6 dialkylamino, C.sub.2-5 acylamino, carboxyl, C.sub.2-5 alkoxycarbonyl and carbamoyl, and R.sup.1 and R.sup.2 independently represent hydrogen atom or C.sub.1-5 alkyl or R.sup.1 and R.sup.2 may form together C.sub.1-5 alkylene, and salts thereof.
    Type: Grant
    Filed: December 6, 1984
    Date of Patent: April 28, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Hiromi Okushima, Akihiro Narimatsu, Makio Kobayashi, Rikizo Furuya, Yoshimi Kitada
  • Patent number: 4659711
    Abstract: Compounds of the general formula ##STR1## and their pharmaceutically-acceptable salts, wherein the substituents are as defined herein, having antihypertensive activity.
    Type: Grant
    Filed: October 4, 1985
    Date of Patent: April 21, 1987
    Assignee: USV Pharmaceutical Corporation
    Inventors: Fu-chin Huang, Howard Jones, Wan-Kit Chan
  • Patent number: 4658026
    Abstract: The present invention relates to new N,N'-bis-(2,3-epoxypropyl) derivatives of cyclic dicarboxylic acid hydrazides and to a process for their production.
    Type: Grant
    Filed: July 31, 1984
    Date of Patent: April 14, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ludwig Rottmaier, Rudolf Merten
  • Patent number: 4656290
    Abstract: A process is disclosed for the preparation of compounds of the Formula IR--X--R.sup.1 (I)wherein X is thio, dithio or carbonyl and R and R.sup.1 are defined hereinbelow which comprises reducing a compound of the Formula IIR--A (II)wherein A is chlorosulfonyl or a group of the Formula ##STR1## with a sulfur compound comprising sulfur which is of the (+)4 oxidation degree and is converted into the (+)6 oxidation degree during the process or with a sulfur compound which is decomposed in acidic medium to a compound of the latter oxidation degree in the presence of a catalytic amount but not more than 0.5 mole--related to 1 mole of the starting material of the Formula II--of elemental iodine or a compound capable of delivering hydrogen iodide in acidic medium or a compound which can be reduced to hydrogen iodide in acidic medium with the sulfur compound used.
    Type: Grant
    Filed: January 16, 1985
    Date of Patent: April 7, 1987
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Istvan Kaldor, Andras Szasz, Ilona Vegh nee Ba, Jozsef Heizer, Eva Behedek nee Haraszin
  • Patent number: 4631276
    Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is a prostaglandin or prostacyclin residue;Y is oxygen, sulfur, imino, or N-(C.sub.1 -C.sub.4 -alkyl) imino;Q is (CR.sub.6 R.sub.7).sub.p wherein p is an integer of 0 to 3;R.sub.2 is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; C.sub.1 -C.sub.4 -alkoxycarbonyl; benzyloxycarbonyl; cyano; or di-C.sub.1 -C.sub.4 -alkylamino-carbonyl;R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 each independently is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; or aryl; andR.sub.3 and R.sub.4 together form a trimethylene, tetramethylene, or 1,3-butadienylene group when R.sub.2 and R.sub.5 together represent a direct bond;have valuable pharmacological properties, e.g., as blood-pressure-lowering or abortive agents.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: December 23, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Walter Elger, Michael-Harold Town, Ekkehard Schillinger
  • Patent number: 4608383
    Abstract: The present invention provides aryloxypropanolamines of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, are hydrogen or halogen atoms or lower alkyl, cyano, carboxamide, hydroxyl, lower acyloxy, lower alkoxy, lower alkenyloxy or aryl lower alkoxy radicals, R.sub.5 and R.sub.6, which may be the same or different, are hydrogen atoms or lower alkyl radicals, X is a straight or branched alkylene chain containing 2 to 6 carbon atoms, A is a mono-, bi- or tricyclic heteroaromatic or hydroheteroaromatic radical or, when at least one of the symbols R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is other than a hydrogen atom, may also be a phenyl radical, with the proviso that when A is a uracil-6-yl radical, the 5-position of the uracil moiety does not contain a hydrogen atom, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.
    Type: Grant
    Filed: October 3, 1983
    Date of Patent: August 26, 1986
    Assignee: Boehringer Mannheim GmbH
    Inventors: Fritz Wiedemann, deceased, Wolfgang Kampe, Karl Dietmann, deceased, Gisbert Sponer
  • Patent number: 4604464
    Abstract: The novel compound, 3-(o-aminobenzoyl)-3,4-dihydrophthalazin-1(2H)-one and novel 3-(substituted aminobenzoyl)-3,4-dihydro-phthalazin-1(2H)-ones, such as 3-(o-methylaminobenzoyl)-3,4-dihydro-phthalazin-1(2H)-one and 3-(o-benzylaminobenzoyl)-3,4-dihydro-phthalazin-1(2H)-one; useful as immunomodulators; and processes for the synthesis of the compounds.
    Type: Grant
    Filed: August 1, 1984
    Date of Patent: August 5, 1986
    Assignee: Pennwalt Corporation
    Inventor: Robert J. Murray
  • Patent number: 4598044
    Abstract: A phenolic compound is used to enhance the sensitivity of a luminescent reaction such as carried out in an immunoassay between a peroxidase enzyme, an oxidant, and a chemiluminescent 2,3-dihydro-1,4-phthalazinedione. Preferably, the phenolic compound is 4-iodophenol, 4-phenylphenol or 2-chloro-4-phenylphenol. In the preferred embodiment, horseradish peroxidase is coupled to an antibody to the substance to be assayed.
    Type: Grant
    Filed: February 9, 1984
    Date of Patent: July 1, 1986
    Assignee: National Research Development Corporation
    Inventors: Larry J. Kricka, Gary H. G. H. Thorpe, Thomas P. Whitehead
  • Patent number: 4590186
    Abstract: The invention relates to cephem compounds of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is amino or protected amino,R.sup.2 is lower aliphatic hydrocarbon group,R.sup.3 is a group of the formula: ##STR2## wherein m is 0 and or 1, andn is 1 or 2,which may have a lower alkyl substituent at the N atom, andX is CH or N,and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: January 10, 1985
    Date of Patent: May 20, 1986
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takao Takaya, Kazuo Sakane, Hideaki Yamanaka
  • Patent number: 4561881
    Abstract: A pollen suppressant of the formula ##STR1## wherein R.sup.1 and R.sup.4 independently represent C.sub.1 -C.sub.4 alkyl, phenyl, naphthyl, or phenyl or naphthyl substituted with one to three substituents selected from the group consisting of halogen, trihalomethyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl, and cyano; R.sup.2 is ##STR2## where R.sup.5 is a C.sub.1 -C.sub.12 alkyl group, optionally substituted with one or more halogen atoms, or an aryl group selected from the group consisting of 6-membered rings containing 0-3 nitrogens and fused bicyclic 10-membered rings containing 6 atoms in each ring and 0-3 nitrogens per ring with the remaining atoms in the ring or rings of said aryl group being carbon atoms, said aryl group being optionally substituted with a C.sub.1 -C.sub.4 alkyl group or an electron-withdrawing group, R.sup.3 is hydrogen, a halogen a C.sub.1 -C.sub.4 alkyl group, a carboxy group or an agronomically acceptable alkali metal salt thereof, or a group of the formula --COOR.sup.
    Type: Grant
    Filed: September 14, 1983
    Date of Patent: December 31, 1985
    Assignee: Lafarge Coppee
    Inventors: Jeffrey N. Labovitz, Lawrence Fang
  • Patent number: 4562201
    Abstract: The present invention relates to new compounds of the formula ##STR1## where X is ##STR2## alkylene, or --S-- where R.sub.1 is hydrogen, alkyl, or aryl; W is hydrogen, hydroxy, amino, alkyloxy, aryloxy, O-alkyl, or O-aralkyl; (Y).sub.A is --CH.sub.2 NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 may be hydrogen, substituted alkyls, aryls, or together with N form a 5 to 7 membered heterocyclic group; and Ar is a substituted or unsubstituted aryl. These compounds are useful in the treatment of various cardiac arrhythmias.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: December 31, 1985
    Assignee: American Hospital Supply Corporation
    Inventors: David M. Stout, William L. Matier
  • Patent number: 4560752
    Abstract: Novel 5-(substituted amino)phenoxyalkyl-, phenylthioalkyl-, phenylsulfinylalkyl-, and phenylsulfonylalkylphosphinates and phosphonates, synthesis thereof, intermediates therefor, and the use of said novel compounds for the control of weeds.
    Type: Grant
    Filed: June 28, 1984
    Date of Patent: December 24, 1985
    Assignee: Zoecon Corporation
    Inventor: Shy-Fuh Lee
  • Patent number: 4532250
    Abstract: Described are compounds of the formula ##STR1## wherein R is heteroaryl and R.sub.1 is hydrogen or loweralkyl, or a pharmaceutically acceptable salt thereof.The compounds exhibit cardiotonic activity.
    Type: Grant
    Filed: November 23, 1983
    Date of Patent: July 30, 1985
    Assignee: American Hospital Supply Corporation
    Inventors: David M. Stout, Diane M. Yamamoto
  • Patent number: 4526968
    Abstract: A aqueous electroplating bath for nickel, cobalt, nickel-cobalt, nickel-iron, cobalt-iron or nickel-cobalt-iron is described which contains, as a brightening agent, a quaternary amine sulfobetaine of the formula ##STR1## wherein N.sup.+ is a heterocyclic tertiary amine group,R is a halogen or lower alkyl group,R' is a hydrogen, lower alkyl or R"C(O)-- groupR" is a lower alkyl group anda is 0-5.These brighteners may be prepared by the reaction of a heterocyclic tertiary amine with an alkali metal halohydrin sulfonate.
    Type: Grant
    Filed: July 16, 1982
    Date of Patent: July 2, 1985
    Assignee: M&T Chemicals Inc.
    Inventors: Kenneth W. Lemke, Maynard W. McNeil
  • Patent number: 4501919
    Abstract: Serine derivatives are synthesized by the condensation of an alkali metal salt of a glycine derivative and a carbonyl compound in the presence of a phase transfer catalyst.
    Type: Grant
    Filed: May 22, 1980
    Date of Patent: February 26, 1985
    Assignee: Gruppo Lepetit S.p.A.
    Inventors: Melvin V. Koch, Ambrogio Magni
  • Patent number: 4477675
    Abstract: The process of preparing a compound of the formula: ##STR1## wherein, Y and Z are each H, alkyl, halo, alkoxy, trifluoromethyl, hydroxy, alkanoyloxy, or alkanoylamino;X is F, Cl, Br, or NR.sub.1 R.sub.2 wherein R.sub.1 and R.sub.2 are each hydrogen, alkyl, alkynyl, alkenyl, cycloalkyl, aryl or aralkyl; andR is H, alkyl, cycloalkyl, or aralkyl; which comprises the step of oxidation of the corresponding 3-desoxy compound.
    Type: Grant
    Filed: September 7, 1982
    Date of Patent: October 16, 1984
    Assignee: USV Pharmaceutical Corporation
    Inventors: Joseph Auerbach, Frederick A. Golec, Jr.
  • Patent number: 4466965
    Abstract: The present invention relates to new compounds of the formula ##STR1## alkylene, or --S-- where R.sub.1 is hydrogen, alkyl, or aryl; W is hydrogen, hydroxy, amino, alkyloxy, aryloxy, O-alkyl, or O-aralkyl; (Y).sub.A is --CH.sub.2 NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 may be hydrogen, substituted alkyls, aryls, or together with N form a 5 to 7 membered heterocyclic group; and Ar is a substituted or unsubstituted heteroaryl. These compounds are useful in the treatment of various cardiac arrhythmias.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: August 21, 1984
    Assignee: American Hospital Supply Corporation
    Inventors: David M. Stout, William L. Matier
  • Patent number: 4464532
    Abstract: A novel process for producing 7-alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone, and its intermediates. 7-Alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone can be obtained by reacting substituted methylenetriphenylphosphorane with 3,5-dimethyl-4-alkoxycarbonylphthalic anhydride to obtain 6-alkoxycarbonyl-5,7-dimethyl-.DELTA..sup.3,.alpha. -substituted methylenephthalide, reacting the latter with hydrazine to obtain a phthalazone derivative, hydrolyzing the latter, halogenating the hydrolyzate to obtain 7-alkoxycarbonyl-6,8-dimethyl-4-(.alpha.-halogeno-.alpha.-substituted methyl)-1-phthalazone and then directly hydrolyzing and decarboxylating the latter or, when said 7-alkoxycarbonyl-6,8-dimethyl-4-(.alpha.-halogeno-.alpha.-substituted methyl)-1-phthalazone is 7-alkoxycarbonyl-6,8-dimethyl-1-phthalazone-4-.alpha.
    Type: Grant
    Filed: June 7, 1982
    Date of Patent: August 7, 1984
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yukio Takei, Masao Yoshida, Rinzo Nishizawa
  • Patent number: 4433148
    Abstract: Compounds are prepared which correspond to the formula ##STR1## wherein R represents a nitrogen containing heterocyclic radical corresponding to one of the formulae ##STR2## each X independently represents chloro, fluoro, bromo, nitro, alkyl of 1 to 4 carbon atoms, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, cyano, trifluoromethyl, trichloromethyl, phenoxy or substituted phenoxy of the formula ##STR3## wherein each Z independently represents chloro, fluoro, bromo, nitro, cyano, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4 carbon atoms, with the proviso that when either n is 2 or 3, all X groups are sterically compatible with each other and all Z groups are sterically compatible with each other; Y represents oxygen or sulfur; each n can independently represent an integer of from 0 to 3, inclusive; R.sup.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: February 21, 1984
    Assignee: The Dow Chemical Co.
    Inventor: Chester E. Pawloski
  • Patent number: 4432978
    Abstract: Derivatives of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]-indole and of (+)enantiomeric, mixtures of (+) and (-)enantiomeric or (.+-.)racemic 2,3,4,4a,5,9b-hexahydro-4a,9b-trans-1H-pyrido[4,3-b]indole, substituted at the 5-position with an aryl group and at the 2-position with a carbonylaminoalkyl group or an aminoalkyl group, are neuroleptic agents useful in the treatment of certain psychoses and neuroses.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: February 21, 1984
    Assignee: Pfizer Inc.
    Inventors: Willard M. Welch, Charles A. Harbert
  • Patent number: 4430171
    Abstract: An aqueous electroplating bath for nickel, cobalt, nickel-cobalt, nickel-iron, cobalt-iron or nickel-cobalt-iron is described which contains, as a brightening agent, a quaternary amine sulfobetaine of the formula ##STR1## wherein N.sup.+ is a heterocyclic tertiary amine group,R is a halogen or lower alkyl group,R' is a hydrogen, lower alkyl or R"C(O)--groupR" is a lower alkyl group anda is 0-5.These brighteners may be prepared by the reaction of a heterocyclic tertiary amine with an alkali metal halohydrin sulfonate.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: February 7, 1984
    Assignee: M&T Chemicals Inc.
    Inventors: Kenneth W. Lemke, Maynard W. McNeil
  • Patent number: 4426387
    Abstract: The invention concerns compounds of formula ##STR1## and acid addition and quaternary ammonium salts thereof, wherein the dotted line represents an optional bond, Ar represents a ring system of formula ##STR2## in which Q is O,S,--CR.sup.7 .dbd.CR.sup.8 --, --N.dbd.CR.sup.8 -- and --N.dbd.N--; R.sup.4, R.sup.5 and R.sup.6, and R.sup.7 and R.sup.8 when present, each represent hydrogen or defined substituents and additionally either R.sup.4 and R.sup.5 when adjacent or R.sup.6 and R.sup.8 when adjacent, together with the carbon atoms to which they are attached also represent a fused five or six membered carbocyclic or heterocyclic ring optionally carrying one or more defined substituents; R is an optionally substituted aryl or heteroaryl radical or a cycloalkyl radical containing 5 to 7 carbon atoms; R.sup.1, R.sup.2, R.sup.3 and R.sup.9 are each hydrogen or a lower alkyl group; n is 0 or 1; X is .dbd.O, .dbd.S or .dbd.NH; Y is --O-- or a direct bond and Z is --CO-- or --CH.sub.
    Type: Grant
    Filed: April 7, 1982
    Date of Patent: January 17, 1984
    Assignee: John Wyeth & Brother Ltd.
    Inventors: John L. Archibald, Terrence J. Ward
  • Patent number: 4413999
    Abstract: The invention provides amidoxime derivatives of the general formula ##STR1## wherein R.sub.1 is an alkyl group of 1 to 8 carbon atoms, phenyl, a heterocyclic ring structure of 5 to 8 atoms containing one or more nitrogen or oxygen atoms or combinations thereof or a bicyclic condensed ring system optionally containing at least one heterocyclic ring which groups may each be optionally substituted. R.sub.2 is a mono or bicyclic heterocyclic radical containing at least two nitrogen atoms which radical is also optionally substituted. R.sub.3 and R.sub.4 are independently H, or an alkyl of 1 to 4 carbon atoms or one, but not both, is ##STR2## and the other, H, wherein R.sub.5 or R.sub.6 are alkyls of 2 to 5 carbon atoms optionally substituted by R.sub.1, or a phenyl optionally substituted by R.sub.1 or R.sub.5 or R.sub.6 is combined with R.sub.1 to jointly form cyclic imidoximes or imidedioximes.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: November 8, 1983
    Assignee: Research Products Rehovot Ltd.
    Inventors: Charles Linder, Gershon Aviv
  • Patent number: 4393062
    Abstract: This invention relates to enzyme inhibitory, novel phthalazin-4-ylacetic acid derivatives of the general formula I: ##STR1## and pharmaceutically acceptable salts as appropriate, to pharmaceutical compositions thereof, and to analogy processes for their manufacture. The compounds of formula I are inhibitors of the enzyme aldose reductase in vivo and as such may be useful in the reduction or prevention of the development of the peripheral effects such as macular oedema, cataract, retinopathy or impaired neural conduction. A preferred compound is 2-(2-fluoro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid.
    Type: Grant
    Filed: October 6, 1980
    Date of Patent: July 12, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventors: David R. Brittain, Robin Wood
  • Patent number: 4385179
    Abstract: The present invention refers to a new process for preparing N-2,3,4,5-substituted-1H-pyrrol-1-yl)-6-substituted amino-3-pyridazineamine, known as antihypertensive agents. The process is characterized in that a suitable 3,6-dihalogenopyridazine is reacted with hydrazine hydrate or other hydrazine derivatives of formula NH.sub.2 NHR, the obtained compound is reacted with a suitable dicarbonyl compound yielding first an alcandione-bis-[6-halogen-3-pyridazininyl]hydrazone, and then a 6-halogen-3-pyrrolylpyridazineamine derivative which is in turn reacted with an amine to yield the desired compounds.
    Type: Grant
    Filed: December 18, 1981
    Date of Patent: May 24, 1983
    Assignee: Gruppo Lepetit S.p.A.
    Inventor: Elvio Bellasio
  • Patent number: 4380547
    Abstract: The invention relates to dihydropyridine compounds of formula (I) as defined in the specification, containing a hetero-ring substituent in the 4-position. Also included in the invention are pharmaceutical compositions containing said compounds of formula (I) and methods for the use of said compounds and compositions. The said compounds are useful for influencing circulation.
    Type: Grant
    Filed: May 29, 1981
    Date of Patent: April 19, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventor: Carsten Materne