Six-membered Hetero Ring Consists Of Oxygen, Nitrogen And Carbon (e.g., 1,2-oxazines, Etc) Patents (Class 544/63)
  • Patent number: 4668690
    Abstract: This invention relates to 1,2,3,4,4a,9b-hexahydro-4a-aminoalkyldibenzofurans of the formula ##STR1## where X is hydrogen, loweralkyl, F and Cl; R.sub.1 is hydrogen, loweralkyl, arylloweralkyl, loweralkenyl, loweralkoxyloweralkyl, aryloxyloweralkyl, cycloalkylloweralkyl and heteroarylloweralkyl: R.sub.2 is hydrogen, lower alkyl or R.sub.1 and R.sub.2 taken together with the N ring atom constitute a saturated or unsaturated heterocyclic ring having 5 or 6 members; R.sub.3 is hydrogen, lower alkyl; n is an interger of 1 to 3; and the pharmaceutically acceptable acid addition salts thereof and where applicable the stereo, optical and geometrical isomers of the foregoing.
    Type: Grant
    Filed: December 30, 1985
    Date of Patent: May 26, 1987
    Assignee: Hoechst Roussel Pharmaceuticals Inc.
    Inventor: Gregory M. Shutske
  • Patent number: 4666902
    Abstract: Tetrahydropyridazinones of the formula I ##STR1## wherein R denotes an optionally substituted carbocyclic or heterocyclic radical, R.sup.1 denotes hydrogen; alkyl; aralkyl, which is optionally substituted in the aryl part; or acyl, and R.sup.2 denotes hydrogen; alkyl, which can optionally be substituted; or optionally substituted phenyl; and their acid addition compounds, if these can be prepared.The tetrahydropyridazinone derivatives of the formula I according to the invention and their physiologically acceptable salts exhibit useful pharmacological actions.
    Type: Grant
    Filed: June 8, 1984
    Date of Patent: May 19, 1987
    Assignee: Cassella Aktiengesellschaft
    Inventors: Gerhard Zoller, Rudi Beyerle, Melitta Just, Piero Martorana, Helmut Bohn, Rolf-Eberhard Nitz
  • Patent number: 4658033
    Abstract: New interphenylene prostaglandin (PGH) analogs are prepared by a method which involves reacting a bicyclic olefin, an acetylene compound and a benzylic halide together, in the presence of a palladium(O) catalyst in a single-step synthesis. By this technique a large number of new interphenylene PGH analogs can be prepared, which are useful as inhibitors of arachidonic acid induced platelet aggregation.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: April 14, 1987
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 4647557
    Abstract: This invention relates to novel heterocyclic derivatives bearing an amino group and to processes for making said compounds.More particularly this invention provides novel heterocyclic compounds the hetero ring of which has two hetero atoms, the same or different, substituted with a free or substituted amino group.These compounds are useful as active ingredients of drugs.
    Type: Grant
    Filed: December 23, 1983
    Date of Patent: March 3, 1987
    Inventors: Gerard Moinet, Michel Schaeffer, Pierre Bessin, Jacqueline Bonnet
  • Patent number: 4645765
    Abstract: New tetracyclo compounds of the formula: ##STR1## in which R.sup.1 is formyl, protected formyl, hydroxymethyl, protected hydroxymethyl, arylaminomethyl, carboxy, protected carboxy or substituted iminomethyl,R.sup.2 is hydroxy, alkoxy or protected hydroxy,R.sup.3 is hydrogen and R.sup.4 is methyl, hydroxymethyl or protected hydroxymethyl, orR.sup.3 and R.sup.4 are combined together to form methylene or oxo,R.sup.5 is hydroxy, alkoxy or protected hydroxy, andR.sup.6 is hydrogen, imino-protective group or alkyl,and pharmaceutically acceptable salts thereof, which have pharmacological activities such as antitumor activity, antimicrobial activity, and the like, and a process for their production and a pharmaceutical composition containing the same.
    Type: Grant
    Filed: June 11, 1985
    Date of Patent: February 24, 1987
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masanobu Kohsaka, Hiroshi Terano, Tadaaki Komori, Morita Iwami, Michio Yamashita, Masashi Hashimoto, Itsuo Uchida, Shigehiro Takase
  • Patent number: 4639436
    Abstract: The invention includes certain 3,4,5-trihydroxypiperidine compounds, methods for their preparation, compositions containing said 3,4,5-trihydroxypiperidine compounds and methods for the use of said compounds and compositions.The subject matter of the invention is useful against diabetes, hyperlipaemia and adiposity as well as in animal nutrition.
    Type: Grant
    Filed: August 23, 1978
    Date of Patent: January 27, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bodo Junge, Hans P. Krause, Lutz Muller, Walter Puls
  • Patent number: 4639286
    Abstract: Azlactone-functional compounds, which are liquid above 20.degree. C., and their method of preparation from alkenyl azlactones and nucleophilic group-substituted compounds are disclosed. The azlactone-functional compounds of the invention cure in the presence of nucleophilic chain-extending or crosslinking agents to form linear or crosslinked polyamide resin systems.
    Type: Grant
    Filed: August 17, 1984
    Date of Patent: January 27, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
  • Patent number: 4624695
    Abstract: The invention relates to novel urease inhibited fertilizer compositions containing urea and a urease inhibiting amount of one or more o-diaminophosphinyl derivatives of oximes, and methods and composition for inhibiting the activity of urease through use of such compounds.
    Type: Grant
    Filed: December 20, 1983
    Date of Patent: November 25, 1986
    Assignee: Allied Corporation
    Inventors: Michael D. Swerdloff, Milorad M. Rogic, Larry L. Hendrickson
  • Patent number: 4596874
    Abstract: A nitrone is synthesized from a secondary amine by reacting a compound represented by the following general formula ##STR1## wherein R.sup.1 and R.sup.2 mean individually a hydrogen atom or an alkyl or aryl group and R.sup.3 denotes an alkyl or aryl group with a peroxide in the presence of a catalyst selected from the group consisting of tungsten compounds, molybdenum compounds, vanadium compounds, titanium compounds, palladium compounds, rhodium compounds, ruthenium compounds and nickel compounds. This process provides the nitrone by one-step oxidation of the secondary amine.
    Type: Grant
    Filed: March 8, 1984
    Date of Patent: June 24, 1986
    Assignee: The President of Osaka University
    Inventors: Shun-Ichi Murahashi, Hitoshi Mitsui
  • Patent number: 4595539
    Abstract: Certain 2-substituted-2-penem-3-carboxylic acid compounds and pharmaceutically-acceptable salts thereof can be prepared from the appropriate xanthate or trithiocarbonate by desulfurization and addition of an electrophilic sulfur compound followed by halogenation and ring closure. The corresponding desulfurized and halogenated olefinic intermediates are disclosed.
    Type: Grant
    Filed: June 10, 1983
    Date of Patent: June 17, 1986
    Assignee: Pfizer Inc.
    Inventor: Ernest S. Hamanaka
  • Patent number: 4579956
    Abstract: Amino-phosphonates are prepared by reacting an enamine with a phosphite ester, for example, according to the equation ##STR1## where OR' is an alcohol moiety and NR.sub.2 is an amino moiety, both R and R' being preferably hydrocarbon such as alkyl or R.sub.2 is part of a ring structure. These compounds have many uses, for example, as corrosion inhibitors, scale inhibitors, fuel stabilizers, etc. In addition, amino-phosphonates can be converted to alpha, beta - unsaturated phosphonates according to the equation ##STR2## which are useful in forming flame retardant polymers and copolymers.
    Type: Grant
    Filed: October 20, 1978
    Date of Patent: April 1, 1986
    Assignee: Petrolite Corporation
    Inventor: Derek Redmore
  • Patent number: 4574153
    Abstract: Antibacterial activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof, wherein, R.sub.1 is an acyl group derived from a carboxylic acid;R.sub.2 is hydrogen, methoxy, or formamido ##STR2## and one of R.sub.3 and R'.sub.3 is hydrogen and the other is ##STR3## and R.sub.4 is hydrogen alkyl, substituted alkyl, phenyl, substituted phenyl, phenylalkyl or (substituted phenyl)alkyl.
    Type: Grant
    Filed: March 1, 1985
    Date of Patent: March 4, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: David Kronenthal, Paula L. Kuester, William H. Koster
  • Patent number: 4569689
    Abstract: Aniline derivatives of the formula ##STR1## where R.sup.1 is alkoxy, alkylthio, unsubstituted or substituted cycloalkoxy or the radical --NR.sup.2 R.sup.3, X is --CH.sub.2 --, --CH(OH)-- or --CO--, A is an unsubstituted or substituted alkylene chain, B is unsubstituted or substituted methylene or dimethylene, Z is hydrogen, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy, and n is 1, 2 or 3, are used for controlling undesirable plant growth.
    Type: Grant
    Filed: June 14, 1984
    Date of Patent: February 11, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Schirmer, Norbert Goetz, Bruno Wuerzer
  • Patent number: 4567276
    Abstract: Novel substituted imidazoles and methods for their preparation are disclosed. These imidazoles, and their salts, exhibit pharmacological activity which includes antihypertensive activity and .beta.-adrenergic blocking activity.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: January 28, 1986
    Assignee: Merck & Co., Inc.
    Inventor: John J. Baldwin
  • Patent number: 4556658
    Abstract: The invention relates to 7-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxyli c acids, processes for their preparation and compositions containing them as antibacterial agents. Also included in the invention are methods for treating bacterial infection using the compounds and compositions of the invention.
    Type: Grant
    Filed: April 24, 1984
    Date of Patent: December 3, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Uwe Petersen, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4555261
    Abstract: This invention relates to a novel class of sulfonamides and their use as herbicides and plant growth regulants.
    Type: Grant
    Filed: November 1, 1984
    Date of Patent: November 26, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Wallace C. Petersen
  • Patent number: 4552585
    Abstract: Compounds of the formula, ##STR1## formulations thereof, and their use as herbicides are disclosed and exemplified.
    Type: Grant
    Filed: October 4, 1984
    Date of Patent: November 12, 1985
    Assignee: FMC Corporation
    Inventor: Jun H. Chang
  • Patent number: 4540703
    Abstract: Tetrazole derivatives of the formula: ##STR1## wherein R.sup.1 is an optional defined substituent; A is sulfur or a lower alkylene-thio; l is 0 or 1; B is a lower alkylene; R.sup.2 is hydroxy, a lower alkoxy, or a group: ##STR2## wherein R.sup.3 and R.sup.4 are optional defined substituents, or the R.sup.3 and R.sup.4 may combine together with the nitrogen atom to which they are joined to form a defined heterocyclic group, and a pharmaceutically acceptable salt thereof, which have prophylactic or therapeutic activities against peptic and/or duodenal ulcers and also anti-inflammatory activity and are useful as an anti-ulcer or anti-inflammatory drug; processes for the preparation of the tetrazole derivatives; and pharmaceutical composition containing said tetrazole derivatives.
    Type: Grant
    Filed: December 23, 1981
    Date of Patent: September 10, 1985
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Minoru Uchida, Takao Nishi, Kazuyuki Nakagawa
  • Patent number: 4536209
    Abstract: .DELTA.'-Tetrahydrophthalimides having a substituted oxy group at 3-position and, if necessary, a halogen atom at 4-position and/or at 2-position of phenyl group as N-substituent have excellent herbicidal activity and are useful as selective herbicides.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: August 20, 1985
    Assignee: Mitsubishi Chemical Industries Ltd.
    Inventors: Tetsuo Jikihara, Masatsugu Oda, Bunji Natsume, Hisao Watanabe, Seiichi Suzuki
  • Patent number: 4535090
    Abstract: 3,5-diphenyl-1H-1,2,4-triazoles with contragestational activity of the following formula ##STR1## wherein R may be located on one or the other of the two adjacent nitrogen atoms and may represent hydrogen or a group R.sub.5 CO-- wherein R.sub.5 is an aliphatic saturated or unsaturated hydrocarbyl containing from 1 to 20 carbon atoms, R.sub.1, R.sub.2 and R.sub.3, each independently are selected from hydrogen, lower alkyl and lower alkoxy or R.sub.2 and R.sub.3 together may represent a methylenedioxy group, and R.sub.4 is an aliphatic saturated or unsaturated hydrocarbyl group of from 1 to 20 carbons, with the proviso that when R is hydrogen or an R.sub.5 CO-- group wherein R.sub.5 contains 4 or less carbon atoms, R.sub.4 must contain 5 or more carbons.These compounds have proven to be highly effective in terminating pregnancy in several animal species after a single parenteral injection.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: August 13, 1985
    Assignee: Gruppo Lepetit S.p.A.
    Inventors: Giulio Galliani, Amedeo Omodei-Sale, Pietro Consonni, Alessandro Assandri
  • Patent number: 4521597
    Abstract: A novel process for producing sulfonylureas of the formula I having a herbicidal action and an action regulating plant growth ##STR1## wherein A is an unsubstituted or substituted phenyl, naphthyl, furan, thiophene or pyridine group, E is a nitrogen atom or the methine group, R.sub.a is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -haloalkyl, C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -haloalkoxy, C.sub.1 -C.sub.5 -alkylthio or C.sub.2 -C.sub.10 -alkoxyalkoxy, and R.sub.b is the same as R.sub.
    Type: Grant
    Filed: October 14, 1983
    Date of Patent: June 4, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Haukur Kristinsson, Werner Topfl
  • Patent number: 4518414
    Abstract: Thiadiazole derivatives of the formula ##STR1## where R.sup.1, A, X, Y, Z, m and n have the meanings given in the description, are used for controlling undesirable plant growth.
    Type: Grant
    Filed: January 11, 1983
    Date of Patent: May 21, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Schirmer, Peter Plath, Bruno Wuerzer
  • Patent number: 4494978
    Abstract: N-(N'-hydrocarbyloxycarbamylalkyl)-2,6-dialkyl-alpha-haloacetanilides have herbicidal activity, particularly in preemergent applications.
    Type: Grant
    Filed: December 30, 1976
    Date of Patent: January 22, 1985
    Assignee: Chevron Research Company
    Inventor: David C. K. Chan
  • 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: 4474746
    Abstract: A radiopharmaceutical chemical compound comprising a radioactive isotope, other than an isotope of iodine, in chemical combination with at least one amine group. The compound has a lipophilicity sufficiently high at a pH of 7.6 to permit passage of the compound from the blood of a mammal into a target organ or tissue and sufficiently low at a pH of 6.6 to prevent rapid return of the compound from the target organ or tissue to the blood. The compound has a percent protein binding of less than ninety percent.A method for selectively depositing a radiopharmaceutical compound in at least one target tissue or organ of a mammal, which tissue or organ has a significantly different intracellular pH than the blood of the mammal, by introducing the compound of the invention into the bloodstream of the mammal.
    Type: Grant
    Filed: July 16, 1982
    Date of Patent: October 2, 1984
    Assignee: State University of New York
    Inventors: Monte Blau, Hank F. Kung
  • Patent number: 4456565
    Abstract: Acyl cyanides of the general formula ##STR1## in which R represents alkyl or substituted alkyl of from 1 to 8 carbon atoms; cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms; aryl or substituted aryl; or an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring, are prepared by reacting the corresponding carboxylic acid anhydride in the liquid phase with anhydrous hydrocyanic acid, at a temperature of between 50.degree. to 250.degree. C.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: June 26, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Herbert Schwarz
  • Patent number: 4440949
    Abstract: A new class of chemical compounds and their process of preparation is described. These compounds have valuable properties as anti-secretory, anti-spasmodic, anti-ulcerogenic and anti-diarrheal agents.
    Type: Grant
    Filed: December 30, 1980
    Date of Patent: April 3, 1984
    Assignee: William H. Rorer, Inc.
    Inventors: George H. Douglas, William L. Studt, Stuart A. Dodson
  • Patent number: 4373102
    Abstract: Novel dyes of the formula ##STR1## where A is cyano, carbo-C.sub.1 -C.sub.4 -alkoxy, carbamyl, N-C.sub.1 -C.sub.4 -alkylcarbamyl, N-phenylcarbamyl, acetyl, benzoyl, 4-nitrophenyl or 4-cyanophenyl,X is hydrogen, chlorine, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, and if n is 2 the substituents may be identical or different,n is 1 or 2,R.sup.1 is hydrogen, methyl, ethyl or 2-hydroxyethyl andR.sup.2 is phenyl or cyclohexyl, orR.sup.1 is hydrogen andR.sup.2 is C.sub.1 -C.sub.4 -alkyl, orR.sup.1 and R.sup.2 are C.sub.1 -C.sub.6 -alkyl, allyl or phenyl-C.sub.1 -C.sub.4 -alkyl orthe group ##STR2## is a saturated heterocyclic five-membered or six-membered ring which may additionally contain an oxygen or a further nitrogen as ring members,Y is hydrogen, hydroxyl, methyl or ethyl; ##STR3## where R.sup.3 is linear or branched C.sub.1 -C.sub.12 -alkyl, or is phenyl; ##STR4## where R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.5 is hydrogen, linear or branched C.sub.1 -C.sub.
    Type: Grant
    Filed: March 7, 1980
    Date of Patent: February 8, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Wolfgang Elser, Gustav Bock, Wolf-Dieter Kermer
  • Patent number: 4356024
    Abstract: A process for the preparation of a 1-amino-1,3,5-triazine-2,4(1H, 3H)-dione compounds comprising the steps of reacting an N-substituted imido-dicarboxylic acid diaryl ester with an isothiosemicarbazone at a temperature of between 50.degree. and 150.degree. C. to form a 1-alkylidene-amino-1,3,5-triazine-2,4(1H, 3H)-dione reaction product; and thereafter, hydrolyzing the reaction product in an acid medium. The reaction product need not be separated from the reaction mixture before the hydrolysis step. Certain novel 1-amino-1,3,5-triazine-2,4(1H, 3H)-dione compounds are provided. The compounds are useful as herbicides.
    Type: Grant
    Filed: February 10, 1981
    Date of Patent: October 26, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karlfried Dickore', Engelbert Kuhle
  • Patent number: 4346088
    Abstract: Thiazoline derivatives of the general formula I ##STR1## wherein R.sup.1 to R.sup.7 have the specified meanings, physiologically acceptable acid addition salts thereof, processes for their preparation, pharmaceutical preparations based on these compounds and their use for acting on the serum lipoprotein spectrum. The invention moreover relates to compounds of the formulae ##STR2## wherein A, R, R.sup.1 to R.sup.7, Y and Z have the specified meanings.
    Type: Grant
    Filed: July 1, 1980
    Date of Patent: August 24, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Jochen Lang, Bernhard Seuring, Ernold Granzer
  • Patent number: 4333929
    Abstract: A compound of formula (II) or a pharmaceutically acceptable acid addition salt thereof ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and each represents C.sub.1-6 alkyl; R.sup.5 represents hydrogen or C.sub.1-6 alkyl; R.sup.6 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.5 and R.sup.6 together represent the remaining members of a 5- or 6-membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl, carboxy or C.sub.1-6 alkoxycarbonyl; and R.sup.7 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: June 8, 1982
    Assignee: Beecham Group Limited
    Inventor: Barrie C. C. Cantello
  • Patent number: 4333936
    Abstract: 5-Benzyl-4-amino-pyrimidine-2-amidines which may or may not be substituted in the phenyl ring, and their physiologically acceptable addition salts with acids, processes for their preparation, drugs containing these compounds, and their use in infectious diseases.
    Type: Grant
    Filed: July 3, 1978
    Date of Patent: June 8, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Scharwaechter, Klaus Gutsche, Wilhelm Kohlmann, Gerhard Kroemer, deceased, by Norma Kroemer, legal representative, by Helmut Kroemer, legal representative, by Maria M. Kroemer, legal representative
  • Patent number: 4331600
    Abstract: Compounds 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 in which R.sub.1 and R.sub.2 are each hydrogen, alkyl, alkenyl, alkynyl, aryl, aralkyl or cycloalkyl; andR is H, alkyl, cycloalkyl or aralkyl; and salts thereof.The compounds have utility as anti-hypertensive and diuretic agents and as intermediates for the preparation of other anti-hypertensive and diuretic agents.
    Type: Grant
    Filed: October 31, 1980
    Date of Patent: May 25, 1982
    Assignee: USV Pharmaceutical Corporation
    Inventors: Frederick A. Golec, Jr., Joseph Auerbach
  • Patent number: 4324792
    Abstract: The present invention provides compounds of the general formula (I) ##STR1## and physiologically acceptable salts and bioprecursors thereof in which ##STR2## represents either ##STR3## R.sup.1 represents hydrogen, halogen, C.sub.1-4 alkoxy, hydroxy, alkyl, R.sup.4 CH(OH)--, cyano or R.sup.5 CONH--, R.sup.2 and R.sup.3, which may be the same or different, each represents a straight or branched chain alkyl group or alkenyl group or R.sup.2 and R.sup.3 may, together with the nitrogen atom to which they are attached, form a saturated heterocyclic ring containing from 5 to 7 members which may optionally contain an oxygen atom; R.sup.4 represents hydrogen or alkyl; and R.sup.5 represents hydrogen, alkyl or C.sub.1-4 alkoxy. The compounds have been shown to exhibit H.sub.1 -antagonist activity in standard pharmacological tests.
    Type: Grant
    Filed: October 3, 1980
    Date of Patent: April 13, 1982
    Assignee: Glaxo Group Limited
    Inventors: John Bradshaw, Alexander W. Oxford, David I. C. Scopes
  • Patent number: 4293549
    Abstract: This invention relates to new compounds, salts, complexes and acylated derivatives thereof, methods of producing said compounds, intermediates used in the method, pharmaceutical compositions containing the present compounds and methods of producing same, and a method of treating patients using the present compounds, having the general formula (I) ##STR1## in which R.sub.1 represents hydrogen, alkyl, alkoxy, hydroxy, halogen, trifluoromethyl, or phenyl; R.sub.2 represents hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, or hydroxy; R.sub.3 represents alkyl, cycloalkyl which can be further mono- or disubstituted with methyl or ethyl, phenyl or phenyl-alkyl, optionally being further substituted; and R.sub.
    Type: Grant
    Filed: October 27, 1978
    Date of Patent: October 6, 1981
    Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktion-saktieselskab)
    Inventors: Schneur Rachlin, Edoardo Arrigoni-Martelli
  • Patent number: 4289765
    Abstract: 4-Aminopyridines of the formula ##STR1## in which R.sup.1 is hydrogen or alkyl of up to 6 carbon atoms andR.sup.2 represents (a) alkyl of up to 6 carbon atoms substituted up to three times with at least one radical from the group of halogen and hydroxyl, with formyl acetalized with an alcohol of up to 3 carbon atoms, alkylthio of up to 3 carbon atoms, phenylthio or the corresponding alkyl- and phenyl-sulfoxy and sulfone groups, the phenyl ring optionally carrying in each case up to three substituents from the group of alkyl, alkyl halide, alkoxy, mono- or dialkylamino having each up to 4 carbon atoms in each alkyl radical, halogen, nitro, amino and hydroxy, or (b) phenylalkyl or diphenyl-alkyl of up to 6 carbon atoms in the linear or branched alkyl moiety, the phenyl rings optionally being substituted up to three times with at least one radical from the group of alkyl, alkoxy, alkyl halide with up to 4 carbon atoms each, halogen, amino, hydroxy, nitro, the sulfamoyl group and the methylene dioxy radical, orR.
    Type: Grant
    Filed: January 7, 1980
    Date of Patent: September 15, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wilfried Greve, Heinzgeorg von Schuh, Hiristo Anagnostopulos
  • Patent number: 4288443
    Abstract: The invention relates to compounds of the general formula ##STR1## and physiologically acceptable salts and N-oxides, hydrates and bioprecursors thereof, in which R.sub.1 and R.sub.2 which may be the same or different each represent hydrogen, C.sub.1-8 alkyl, C.sub.4-8 cycloalkyl, C.sub.3-6 alkenyl, aralkyl with 1 to 4 carbon atoms in the alkyl residue or C.sub.1-8 alkyl interrupted by an oxygen atom or a group ##STR2## in which R.sub.5 represents hydrogen or C.sub.1-8 alkyl, or R.sub.1 and R.sub.2 may together with the nitrogen atom to which they are attached, form a saturated monocyclic 5 to 7 membered heterocyclic ring which may additionally contain the heterofunction O or ##STR3## R.sub.3 represents straight or branched chain C.sub.1-8 alkyl, alkoxyalkyl with 1 to 8 carbon atoms in each alkyl residue, C.sub.1-8 hydroxyalkyl, C.sub.1-8 alkoxycarbonyl, alkyl thioalkyl with 1 to 8 carbon atoms in each alkyl residue, halogen or aryl;R.sub.4 represents hydrogen, C.sub.1-8 alkyl, C.sub.
    Type: Grant
    Filed: February 25, 1980
    Date of Patent: September 8, 1981
    Assignee: Glaxo Group Limited
    Inventors: Duncan B. Judd, John W. Clitherow, Barry J. Price, John Bradshaw
  • Patent number: 4288437
    Abstract: Compounds of the formula ##STR1## wherein Ar is phenyl; mono- or di-substituted phenyl, where the substituents are one to two halogens, one to two alkyls of 1 to 3 carbon atoms, or one amino, nitro, cyano or trifluoromethyl; or pyridinyl;R is hydrogen, chlorine, methyl or methoxy;R.sub.1 is hydrogen or methyl;R.sub.2 is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, methyl-(cycloalkyl of 3 to 8 carbon atoms) or --A--R.sub.4,where A is alkylene of 2 to 3 carbon atoms, and R.sub.4 is hydroxyl, methylamino, dimethylamino, N-methyl-ethylamino, diethylamino, pyrrolidino, piperidino, hexamethyleneimino, morpholino or 4-methyl-1-piperazinyl; orR.sub.1 and R.sub.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: September 8, 1981
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Wolfhard Engel, Gunter Trummlitz, Ernst Seeger, Joachim Kahling
  • Patent number: 4279928
    Abstract: Multiple daily dosing with amidinoureas of the formula ##STR1## produces a significant and sustained decrease in blood pressure in humans.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: July 21, 1981
    Assignee: William H. Rorer, Inc.
    Inventors: Richard L. Riley, George H. Douglas, John Yelnosky
  • Patent number: 4279902
    Abstract: Acetamide derivatives are provided having the structure ##STR1## wherein X is a single bond, --CH.sub.2 -- or --O--, R.sup.1 and R.sup.2 may be the same or different and are lower alkyl, phenyl-lower alkoxy-lower alkyl, lower alkenyl, phenyl-lower alkyl or lower alkoxy, or ##STR2## may be taken together to form a 5- to 7-membered heterocyclic ring optionally containing one other hetero atom, such as nitrogen, sulfur or oxygen; Y is hydroxyl, OR wherein R is lower alkyl, lower alkenyl or lower alkanoyl, or ##STR3## wherein R.sup.1 and R.sup.2, and R.sup.1 and R.sup.2 taken together with the nitrogen to which they are attached are as defined above, and n is 1 to 6.These compounds are useful as anti-arrhythmia agents and have been found to be effective in the treatment of acute myocardial infarction.
    Type: Grant
    Filed: August 6, 1980
    Date of Patent: July 21, 1981
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Frederic P. Hauck, Glenn A. Jacobs
  • Patent number: 4279905
    Abstract: Novel, 3-amino-1-benzoxepin-5 (2H)-one derivatives and methods for their production are disclosed. These derivatives correspond to the Formula I: ##STR1## wherein: R.sub.1 and R.sub.2 independently of one another arehydrogen,C.sub.1 -C.sub.5 alkyl,C.sub.1 -C.sub.5 alkyl substituted with a terminal phenyl, or a phenyl containing one or two halogens, methyl or methoxy groups, a 3,4-methylenedioxy or a 3,4-ethylenedioxy group,C.sub.2 -C.sub.5 alkyl substituted with terminal hydroxy or methoxy or,C.sub.3 -C.sub.4 alkenyl; orone of R.sub.1 and R.sub.2 are hydrogen or a C.sub.1 -C.sub.5 alkyl and the other is a C.sub.2 -C.sub.5 alkyl substituted with a terminal NR.sub.5 R.sub.6 ;R.sub.5 and R.sub.6 independently of one another are hydrogen or C.sub.1 -C.sub.5 alkyl; orR.sub.5 and R.sub.6 are together a 5 to 7 member ring, orR.sub.5 and R.sub.6 are together a 5 to 7 member ring having heterogeneous oxygen, sulfur or nitrogen;R.sub.1 and R.sub.2 are together a 5 to 7 member ring, orR.sub.1 and R.sub.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: July 21, 1981
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Heinrich-Wilhelm Ohlendorf, Klaus-Ullrich Wolf, Wilhelm Kaupmann
  • Patent number: 4279904
    Abstract: Novel 3-amino-1-benzoxepine derivatives and methods for their production are disclosed. These derivatives correspond to the Formula I ##STR1## wherein: R.sub.1 and R.sub.2 independently of one another arehydrogen,C.sub.1 -C.sub.5 alkyl,C.sub.1 -C.sub.5 alkyl substituted with a terminal phenyl, or a phenyl containing one or two halogens, methyl or methoxy groups, a 3,4-methylenedioxy or a 3,4-ethylenedioxy group,C.sub.2 -C.sub.5 alkyl substituted with terminal hydroxy or methoxy or,C.sub.3 -C.sub.4 alkenyl; orone of R.sub.1 and R.sub.2 are hydrogen or a C.sub.1 -C.sub.5 alkyl and the other is a C.sub.2 -C.sub.5 alkyl substituted with a terminal NR.sub.7 R.sub.8 ;R.sub.7 and R.sub.8 independently of one another are hydrogen or C.sub.1 -C.sub.5 alkyl; orR.sub.7 and R.sub.8 are together a 5 to 7 member ring or said ring having heterogeneous oxygen, sulfur or nitrogen, orR.sub.1 and R.sub.2 are together a 5 to 7 member ring or said ring having heterogeneous oxygen, sulfur or NR.sub.9 ;R.sub.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: July 21, 1981
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Heinrich-Wilhelm Ohlendorf, Klaus-Ullrich Wolf, Wilhelm Kaupmann, Henning Heinemann
  • Patent number: 4275209
    Abstract: The present invention relates to novel thioxanthene and xanthene derivatives which have useful pharmacodynamic activity, such as neuroleptic activity and antiemetic activity, methods for the preparation of said derivatives, pharmaceutical compositions containing same, and a method for the treatment of psychic disorders by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.
    Type: Grant
    Filed: December 21, 1979
    Date of Patent: June 23, 1981
    Assignee: Kefalas A/S
    Inventors: Niels Lassen, Klaus P. Bogeso, Peter B. Hansen, Jorn L. M. Buus, Allan J. Bigler
  • Patent number: 4247556
    Abstract: There are prepared 7-azabenzimidazoles of the formula ##STR1## where R.sub.1 and R.sub.2 are the same or different and are hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.6 -alkanol or --NR.sub.1 R.sub.2 is a 5 to 7 membered saturated heterocyclic ring having either one nitrogen atom, one nitrogen atom and one oxygen atom or two nitrogen atoms, R.sub.3 is hydroxy, an amino group, a mono C.sub.1 -C.sub.6 -Alkylamino group, a di-C.sub.1 -C.sub.6 -alkylamino group, or a C.sub.2 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, mercapto, C.sub.1 -C.sub.6 -alkylmercapto, hydroxy or C.sub.1 -C.sub.6 -alkoxy, R.sub.5 is hydrogen or halogen and A is a C.sub.2 -C.sub.6 -alkylene group or a salt of such compound. Preferably R.sub.1 and R.sub.2 are two equal C.sub.1 -C.sub.6 -alkyl groups or --NR.sub.1 R.sub.2 is piperidino, pyrrolidino, morpholino, homopiperidino, piperazino or homopiperazino, R.sub.3 is hydroxy, mercapto, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylmercapto or C.sub.1 -C.sub.
    Type: Grant
    Filed: January 15, 1979
    Date of Patent: January 27, 1981
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Walter von Bebenburg, Istvan Szelenyi, Klaus Thiemer
  • Patent number: 4238412
    Abstract: Acyl cyanides of the general formula ##STR1## in which R represents alkyl or substituted alkyl of from 1 to 8 carbon atoms; cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms; aryl or substituted aryl; or an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring,are prepared by reacting the corresponding carboxylic acid anhydride with an alkali metal cyanide or anhydrous hydrocyanic acid, at a temperature of between 50.degree. and 250.degree. C. and the resulting acyl cyanide is removed from the reaction medium by distillation, immediately after it has been formed.
    Type: Grant
    Filed: December 8, 1978
    Date of Patent: December 9, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Herbert Schwarz
  • Patent number: 4199590
    Abstract: Compounds of formula ##STR1## in which hal represents halogen;R represents hydrogen or lower alkyl having 1 to 6 carbon atoms;R.sup.2 represents a subsituted or unsubstituted monocyclic heterocyclic group;and X represents oxygen or sulphur; or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof, are disclosed which have hypotensive and/or antihypertensive activity.
    Type: Grant
    Filed: August 24, 1978
    Date of Patent: April 22, 1980
    Assignee: John Wyeth & Brother Limited
    Inventor: Terence J. Ward
  • Patent number: 4154828
    Abstract: N.sup.2 -naphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis.
    Type: Grant
    Filed: October 21, 1977
    Date of Patent: May 15, 1979
    Assignees: Mitsubishi Chemical Industries, Ltd., Shosuke 0KAMOTO
    Inventors: Shosuke Okamoto, Ryoji Kikumoto, Yoshikuno Tamao, Kazuo Ohkubo, Shinji Tonomura
  • Patent number: 4139529
    Abstract: N.sup.2 -naphthalenesulfonyl-L-arginine esters and amides and the pharmaceutically acceptable acid addition salts thereof which have antithrombotic properties.
    Type: Grant
    Filed: August 31, 1977
    Date of Patent: February 13, 1979
    Assignees: Mitsubishi Chemical Industries Limited, Shosuke Okamoto
    Inventors: Shosuke Okamoto, Akiko Hijikata, Hyogi Kikumoto, Yoshikuni Tamao, Kazdo Ohkubo, Tohru Tezuka, Shinji Tonomura
  • Patent number: 4137304
    Abstract: Cyclic and acyclic amides, substituted ureas and sulphonamides are disclosed having the property of stimulating the cold receptors of the nervous system of the body to produce a cold sensation and are used for this purpose in a variety of edible and topical preparations.
    Type: Grant
    Filed: June 2, 1977
    Date of Patent: January 30, 1979
    Assignee: Wilkinson Sword Limited
    Inventors: David G. Rowsell, Roger Hems
  • Patent number: 4133880
    Abstract: N.sup.2 -substituted-L-arginine esters and amides, and the pharmaceutically acceptable acid addition salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis.
    Type: Grant
    Filed: July 28, 1977
    Date of Patent: January 9, 1979
    Assignees: Mitsubishi Chemical Industries Ltd., Shosuke Okamoto
    Inventors: Shosuke Okamoto, Akiko Hijikata, Ryoji Kikumoto, Yoshikuni Tamao, Kazuo Ohkubo, Tohru Tezuka, Shinji Tonomura