Patents Examined by W. B. Springer
  • Patent number: 4820835
    Abstract: A compound of the formula: ##STR1## wherein T is tritium; is described as well as intermediates for its preparation. The compound of formula I is useful in an assay for detecting the presence of benzodiazepine receptor occupiers in a warmblooded animal.
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: April 11, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Walter Burger, Arnold A. Liebman, Clark W. Perry
  • Patent number: 4797415
    Abstract: A new series of benzofuran and benzothiophene derivatives are disclosed. These compounds have a structure which can be obtained by substituting the third position of 2-lower alkyl-benzofuran or 2-lower alkyl-benzothiophene with a substituted benzene derivative, itaconic acid derivative or a substituted phenoxymethyl tetrazole derivative. They are useful as diuretics without side effects of elevating serum uric acid levels and can be used in the treatment of hyperuricemia.
    Type: Grant
    Filed: July 28, 1986
    Date of Patent: January 10, 1989
    Assignee: Kotobuki Seiyaku Company Limited
    Inventors: Tsuyoshi Tomiyama, Akira Tomiyama, Koichi Kubota
  • Patent number: 4780546
    Abstract: A method for the production of maleimides, which comprises subjecting maleinamic acids to ring-closure imidation in an organic solvent capable of forming an azeotrope with water in the presence of an acid catalyst at a temperature in the range of 120.degree. C. to 250.degree. C. while removing the formed water in the form of an azeotrope with said organic solvent and thereafter purifying the produced maleimides.
    Type: Grant
    Filed: October 27, 1986
    Date of Patent: October 25, 1988
    Assignee: Nippon Shokubai Kagaku Kogyo Co. Ltd.
    Inventors: Yuichi Kita, Kentaro Sakamoto, Masao Baba, Atsushi Okubo
  • Patent number: 4751298
    Abstract: There is disclosed a process for the production of 1,4-bis-[3-(3,4,5-trimethoxybenzyloxy)-propyl]-diazepane which consists of first reacting 3-aminopropanol with acrylonitrile and subsequently reacting in aqueous solution with formaldehyde and hydrocyanic acid or with formaldehyde and an alkali cyanide in the presence of alkali hydrogen sulfite to form cyanomethyl-(2-cyano-ethyl)-(3-hydroxy-propyl)-amine; hydrogenating the thus obtained reaction product in the presence of a hydrogenating catalyst and ammonia to 1 (3-hydroxy-propyl)-1,4-diazepane and reacting the latter compound for example with 3-halogen propanol or with allyl alcohol and introducing two 3,4,5-trimethoxy-benzoyl groups into the thus obtained reaction product by esterification.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: June 14, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Axel Kleemann, Bernd Lehmann, Klaus Deller
  • Patent number: 4708961
    Abstract: The present invention is concerned with novel acylindole derivatives of the formula (I) and platelet-aggregation inhibiting agents containing them as an active ingredient. ##STR1## In the formula (I), either R.sub.1 and R.sub.2 is hydrogen, an alkyl group having 1 to 5 carbon atoms, an alkyl group substituted by at least one hydroxy group and having 1 to 5 carbon atoms, or a group of the formula ##STR2## in which R.sub.3 is an alkyl group having 1 to 5 carbon atoms, and --OR.sub.2 is a substituent at the ortho or para position.The compounds of the invention are useful as preventive medicine or remedy for various diseases or symptoms caused by platelet-aggregation, as well as inhibitors of platelet-aggregation on vascular walls during or after an operation.
    Type: Grant
    Filed: October 16, 1986
    Date of Patent: November 24, 1987
    Inventors: Kazuharu Ienaga, Ko Nakamura
  • Patent number: 4675414
    Abstract: Aliphatic polyethers having at least two N-methylmaleimide groups chemica joined thereto by a carbonate linkage are provided and a method for making such compounds. The hydroxy-terminated aliphatic polyether, such as polypropylene glycol, is initially reacted with carbonyl chloride to form the chloroformate. The polyether chloroformate derivative is then reacted with N-hydroxymethylmaleimide yielding the bis or tris(maleimidomethyl)carbonate of said polyether.
    Type: Grant
    Filed: March 8, 1985
    Date of Patent: June 23, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Albert A. DeFusco, Eugene C. Martin
  • Patent number: 4652659
    Abstract: 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid carboxymethyl ester as known per se is obtainable by a novel and more simple method comprising mild acid hydrolysis of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxyacetic tetrahydropyran-2-yl ester. The final product is a valuable drug having antiinflammatory activity.
    Type: Grant
    Filed: October 16, 1984
    Date of Patent: March 24, 1987
    Assignee: Siegfried Aktiengesellschaft
    Inventors: Rene Gnehm, Rolf Weber
  • Patent number: 4623377
    Abstract: Tetrahydroquinolin-1-ylcarbonylimidazoles of the formula ##STR1## in which n is 0, 1, 2 or 3,which possess herbicidal and fungicidal activity. The corresponding intermediates of the formula ##STR2## are also new.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: November 18, 1986
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Yoshio Kurahashi, Kozo Shiokawa, Toshio Goto, Shinzo Kagabu, Atsumi Kamochi, Koichi Moriya, Hidenori Hayakawa
  • Patent number: 4605664
    Abstract: The invention relates to novel substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones, their analogs and their salts. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful for the treatment and prevention of injury to the brain and of edema due to head trauma, stroke (particularly ischemic), arrested breathing, cardiac arrest, Reye's syndrome, cerebral thrombosis, cerebral embolism, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections and various brain concussions.
    Type: Grant
    Filed: May 1, 1984
    Date of Patent: August 12, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
  • Patent number: 4596821
    Abstract: The invention relates to novel substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones, their analogs and their salts. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful for the treatment and prevention of injury to the brain and of edema due to head trauma, stroke (particularly ischemic), arrested breathing, cardiac arrest, Reye's syndrome, cerebral thrombosis, cerebral embolism, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections and various brain concussions.
    Type: Grant
    Filed: May 1, 1984
    Date of Patent: June 24, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
  • Patent number: 4452738
    Abstract: The invention relates to a process for the manufacture of the known 5-carbamoyl-10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine of the formula III which is characterized in that, for example, 5-cyano-5H-dibenz[b,f]azepine of the formula I is nitrated to form 5-cyano-10-nitro-5H-dibenz[b,f]azepine of the formula II, this is subjected to hydrolysis, then reduction, then the reduction product contained in the reaction mixture is subjected to hydrolysis and the end product of the formula III is isolated in pure form.The process is illustrated by the following reaction scheme: ##STR1## The invention relates also to new intermediates produced in these reactions.
    Type: Grant
    Filed: May 26, 1983
    Date of Patent: June 5, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Ernst Aufderhaar
  • Patent number: 4434176
    Abstract: This invention provides compounds of formula I, ##STR1## wherein R.sub.1 is phenyl; phenyl monosubstituted with fluorine; phenyl mono- or disubstituted with chlorine; phenyl mono-, di- or trisubstituted with methyl or methoxy, secondary 1-phenoxyalkyl, the secondary alkyl residue of which is of 3 to 5 carbon atoms and in which the phenyl residue is unsubstituted or monosubstituted with chlorine, andeither R.sub.2 is hydrogen,and R.sub.3 is methyl,or R.sub.2 is methyland R.sub.3 is hydrogen or methyl,which are useful, for example, for treating coronary conditions.
    Type: Grant
    Filed: May 6, 1982
    Date of Patent: February 28, 1984
    Assignee: Sandoz Ltd.
    Inventors: Franz Troxler, Fritz Seemann
  • Patent number: 4432902
    Abstract: A method and apparatus for electrochemically synthesizing N.sub.2 O.sub.5 cludes oxidizing a solution of N.sub.2 O.sub.4 /HNO.sub.3 at an anode, while maintaining a controlled potential between the N.sub.2 O.sub.4 /HNO.sub.3 solution and the anode. A potential of about 1.35 to 2.0 V vs. SCE is preferred, while a potential of about 1.80 V vs. SCE is most preferred. Thereafter, the N.sub.2 O.sub.5 is reacted with either 1.5-diacetyl-3,7-dinitro-1,3,5,7-tetraazacyclooctane (DADN) or 1,3,5,7-tetraacetyl-1,3,5,7-tetraazacyclooctane (TAT) to form cyclotetramethylenetetraamine (HMX).
    Type: Grant
    Filed: July 20, 1982
    Date of Patent: February 21, 1984
    Assignee: The United States of America as represented by the Department of Energy
    Inventors: Raymond R. McGuire, Clifford L. Coon, Jackson E. Harrar, Richard K. Pearson
  • Patent number: 4431660
    Abstract: Novel 4-substituted-3-hydroxy-3-pyrroline-2,5-diones are disclosed which inhibit glycolic acid oxidase and thus are useful in the treatment and prevention of calcium oxalate renal lithiasis.
    Type: Grant
    Filed: October 17, 1980
    Date of Patent: February 14, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Clarence S. Rooney, Haydn W. R. Williams
  • Patent number: 4380640
    Abstract: The invention discloses novel herbicidally active and plant growth-regulating benzthiazolylurea derivatives of the formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 -alkylnyl or C.sub.3 -C.sub.6 cycloalkyl; R.sub.2 has the same meaning as R.sub.1 or is C.sub.1 -C.sub.6 alkoxy; R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, also form a 5- to 6-membered heterocyclic ring which can be substituted by C.sub.1 -C.sub.3 alkyl; R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, an alkali metal cation or an alkaline earth metal cation or a C.sub.1 -C.sub.4 alkylammonium radical, the alkyl moieties of which can be substituted by OH, NH.sub.2, CN or C.sub.1 -C.sub.4 alkoxy; R.sub.5 to R.sub.9 are preferably hydrogen or C.sub.1 -C.sub.4 alkyl, but can also have one of the other meanings defined more closely in the specification; X.sub.1 and X.sub.2, each independently of the other, is a C.sub.1 -C.sub.8 alkoxy or C.sub.1 -C.sub.
    Type: Grant
    Filed: January 12, 1981
    Date of Patent: April 19, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Georg Brunner, Werner Fory
  • Patent number: 4327215
    Abstract: The present invention relates to a simplified process, which avoids organo-lithium intermediates, for the preparation of erythro-.alpha.-piperid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl-metha nol, wherein 2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid or a salt thereof is reacted with a pyrid-2-yl-magnesium halide to give pyrid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl ketone in the manner of a Grignard reaction, and this product is hydrogenated, in a conventional manner, to give erythro-.alpha.-piperid-2-yl-2,8-bis-(trifluoromethyl)-quinolin-4-yl-metha nol.
    Type: Grant
    Filed: October 3, 1980
    Date of Patent: April 27, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Hickmann, Heinz-Guenter Oeser, Leander Moebius
  • Patent number: 4322417
    Abstract: Polyfluorohydroxyisopropyl tricyclic carbostyrils, such as 2,3-dihydro-7-methyl-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl ]-5H-[1,4]thiazino[2,3,4-ij]-quinolin-5-one, useful as antihypertensive agents.
    Type: Grant
    Filed: December 22, 1977
    Date of Patent: March 30, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Paul E. Aldrich, Gilbert H. Berezin
  • Patent number: 4301290
    Abstract: Decahydro or octahydro-4-phenyl-cis-isoquinoline derivatives are useful as analgesics, anti-depressants, tranquilizers and sleep inducers.
    Type: Grant
    Filed: March 7, 1979
    Date of Patent: November 17, 1981
    Assignee: Sandoz Ltd.
    Inventors: Paul Pfaffli, Hartmut Hauth
  • Patent number: 4287344
    Abstract: The present invention relates to novel derivatives of imidazolin-2-thione and a method of preparing same. These novel compounds comprise N,N'-bis-substituted imidazolin-2-thiones of the formula: ##STR1## wherein R.sub.1 is ##STR2## R.sub.2 is hydrogen or methyl. The method of preparing said compounds according to the present invention comprises reacting imidazolin-2-thione with formaldehyde and a compound of the formula: ##STR3## wherein R.sub.2 is hydrogen or methyl, at the molar ratio therebetween of 1:2:2 respectively in an aqueous medium or in a medium of polar organic solvents at a temperature ranging from 20.degree. to 80.degree. C. The method according to the invention makes it possible to obtain the desired product at a high yield (up to 93% of the theoretical value).
    Type: Grant
    Filed: August 3, 1977
    Date of Patent: September 1, 1981
    Inventors: Abidzhan Safaev, Abduvasit Kadyrov, Zhakhongir G. Saidaliev, Tulyagan F. Faiziev
  • Patent number: 4284556
    Abstract: A group of 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines whose structures have amino, hydroxy substituents at the 7,8-positions of the benzazepine nucleus is disclosed. Novel intermediates and routes of synthesis used for preparing them are also described. The end products have pharmacodynamic activity.
    Type: Grant
    Filed: January 31, 1980
    Date of Patent: August 18, 1981
    Assignee: SmithKline Corporation
    Inventors: Kenneth G. Holden, Carl Kaiser, Joseph Weinstock