Four Or More Ring Nitrogens In The Tricyclo Ring System Patents (Class 544/251)
  • Patent number: 5216159
    Abstract: The invention encompasses a compound of the formula ##STR1## and the pharmaceutically acceptable non-toxic salts thereof wherein X, W, Y, R, and R2 are variables.These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine type drugs, and enhancement of alertness.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: June 1, 1993
    Assignee: Neurogen Corporation
    Inventors: Andrew Thurkauf, Alan J. Hutchison, Vinod Singh
  • Patent number: 5212310
    Abstract: The present invention encompasses structures of the formula: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof wherein: ##STR2## and W, X, A, B, C, D, E, R.sub.3, R.sub.4 are variables. These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine drugs, and enhancement of memory.
    Type: Grant
    Filed: December 19, 1991
    Date of Patent: May 18, 1993
    Assignee: Neurogen Corporation
    Inventors: Andrew Thurkauf, Alan Hutchison, Pamela Albaugh
  • Patent number: 5210023
    Abstract: A method of purifying ferment-produced riboflavin, wherein the impure riboflavin is suspended in water or dilute aqueous acid, and the suspension is heated at a temperature of from 75.degree. to 130.degree. C. for from 0.3 to 3 hours with stirring, during which time crystal transformation takes place, after which the mixture is cooled and the purified product is isolated in known manner.
    Type: Grant
    Filed: July 1, 1991
    Date of Patent: May 11, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Grimmer, Hans Kiefer, Christoph Martin
  • Patent number: 5196533
    Abstract: 6,6-Disubstituted pteridines which are useful for the regulation of enzymes are disclosed, along with a general method of synthesizing these compounds.
    Type: Grant
    Filed: March 14, 1991
    Date of Patent: March 23, 1993
    Assignee: South Alabama Medical Science Foundation, USA
    Inventors: June E. Ayling, Steven W. Bailey
  • Patent number: 5180824
    Abstract: This invention pertains to novel methods of synthesizing fludarabine, fludarabine phosphate and related nucleoside pharmacologic agents utilizing 6-azido-2-fluoropurine as a novel intermediate.In particular this invention pertains to a synthesis of fludarabine where the relatively low yield fluorination step is done before the costly coupling step.
    Type: Grant
    Filed: November 29, 1990
    Date of Patent: January 19, 1993
    Assignee: Berlex Biosciences Inc.
    Inventors: John G. Bauman, Randolph C. Wirsching
  • Patent number: 5173492
    Abstract: There are disclosed s-triazolo[3,4-i]purine derivatives represented by formula: ##STR1## wherein Y-Z represents ##STR2## R.sub.4 represents hydrogen, alkyl, substituted or unsubstituted aromatic heterocyclic group or substituted or unsubstituted aryl; and X.sup.2 represents oxygen, sulfur or NH; each of R.sup.1 and R.sup.2 independently represents hydrogen, alkyl, cycloalkyl, aralkyl or substituted or unsubstituted aryl; R.sup.3 represents alkyl, cycloalkyl, aralkyl or substituted or unsubstituted aryl; X.sup.1 represents oxygen or sulfur; and represents a single bond or a double bond or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: August 23, 1991
    Date of Patent: December 22, 1992
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Fumio Suzuki, Junichi Shimada, Kenji Ohmori, Haruhiko Manabe, Kazuihiro Kubo, Akira Karasawa, Tetsuji Ohno, Shizuo Shiozaki, Akio Ishii, Katsuichi Shuto
  • Patent number: 5155112
    Abstract: The present invention provides the compounds of formula (I) ##STR1## and salts and solvates thereof wherein R.sup.1 represents a hydrogen or fluorine atom or a hydroxy group, R.sup.2 represents a fluorine atom or a hydroxyl or C.sub.1-6 alkoxy group and B represents a purine base, and describes processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of viral infections, particularly those caused by the Herpetoviridae.
    Type: Grant
    Filed: November 23, 1990
    Date of Patent: October 13, 1992
    Assignee: Glaxo Group Limited
    Inventors: Richard Storer, Ian L. Paternoster, Alan D. Borthwick, Keith Biggadike
  • Patent number: 5132424
    Abstract: New pyrazolo-pyrrolo-pyrimidine-dione (PPPD) compounds of formula (I), ##STR1## where R.sub.1, R.sub.2, R.sub.3, R.sub.4 and m are as defined in the specification, e.g., 4-(benzoylmethyl)-6-cyclohexyl-6,7-dihydro-2-phenyl-4H-pyrazolo[1,5-a]pyrr olo[3,4-d]pyrimidine-5,8-dione, have been found to be potentially useful to treat warm-blooded animal patients suffering from the symptoms of atherosclerosis and cholesterol buildup to relieve the same and for favorably altering the high density lipoprotein (HDL) to low density lipoprotein (LDL) ratio in blood samples of such patients.
    Type: Grant
    Filed: January 21, 1991
    Date of Patent: July 21, 1992
    Assignee: The Upjohn Company
    Inventors: Scott D. Larsen, Frank P. Bell
  • Patent number: 5116843
    Abstract: The present invention provides tricyclic benzimidazoles of the formula ##STR1## wherein R.sub.1 is a phenyl radical of the general formula: ##STR2## wherein R.sub.2, R.sub.3 and R.sub.4 can be the same or different as in claim 1. For A, B, C and D are understood those compounds where one or two of A, B, C or D are nitrogen. These compounds are useful to inhibit the aggregation of thrombocytes and erythrocytes, lower blood pressure and can increase the power of the heart.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: May 26, 1992
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Wolfgang von der Saal, Erwin Boehm, Klaus Strein
  • Patent number: 5110926
    Abstract: A process is described for the preparation of carbocyclic guanosine from aristeromycin in a multi-step procedure, the final step of which is the hydrolysis of a compound of the formula ##STR1## wherein R.sup.1 represents a C.sub.1-6 alkyl group or an arylC.sub.1-4 alkyl group and R.sup.2, R.sup.3 and R.sup.4 each independently represent a hydrogen atom or a hydroxyl protecting group.Carbocyclic guanosine is an intermediate in the synthesis of carbocyclic analogues of nucleosides having use in therapy, particularly as antiviral agents.
    Type: Grant
    Filed: July 18, 1990
    Date of Patent: May 5, 1992
    Assignee: Glaxo Group Limited
    Inventors: Richard Storer, Chi L. Mo, John P. Turnbull
  • Patent number: 5103005
    Abstract: A method for the recovery of riboflavin from a fermentation broth or other feed stock is disclosed. The method comprises a process for the production of large, pure riboflavin crystals from an alkaline, aqueous solution containing solubilized riboflavin. The method can further comprise the process for production of large, pure riboflavin crystals in combination with two solids/liquid separation steps, the latter of which can result in a final riboflavin product purity of at least about 96% by weight.
    Type: Grant
    Filed: July 21, 1989
    Date of Patent: April 7, 1992
    Assignee: Coors Biotech, Inc.
    Inventors: Dale C. Gyure, George W. Lauderdale
  • Patent number: 5101032
    Abstract: Cycloalkylidene dyes have the formula ##STR1## where m is 0 or 1,L is a chemical bond or C.sub.1 -C.sub.2 -alkylene, which may be substituted,R.sup.1 is hydrogen, C.sub.1 -C.sub.20 -alkyl, which may be phenyl-substituted, substituted or unsubstituted phenyl, naphthyl or C.sub.3 -C.sub.7 -cycloalkyl,Y is oxygen or two hydrogens,X.sup.1 is oxygen andX.sup.2 is C.sub.1 -C.sub.8 -alkanoyloxy, substituted or unsubstituted benzoyloxy, C.sub.1 -C.sub.6 -trialkylsilyloxy or a radical of the formula OR.sup.1 or NR.sup.2 R.sup.3, where R.sup.1 is as defined above and R.sup.2 and R.sup.3 are identical or different and each is independently of the other C.sub.1 -C.sub.20 -alkyl, which may be phenyl-substituted, substituted or unsubstituted phenyl, naphthyl, or C.sub.3 -C.sub.7 -cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom joining them are saturated heterocyclyl, or else one of R.sup.2 and R.sup.3 is hydrogen, or X.sup.1 and X.sup.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Dieter Martin, Bernhard Albert, Knut Kessel
  • Patent number: 5095015
    Abstract: The invention encompasses compounds of the formula: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof where n is 0, 1, or 2 and x is ##STR2## and R.sub.1, R.sub.2, R.sub.3, Y, Z, W, T are defined variables. These compounds are highly selective agonists or inverse agonists for the GABAa brain receptors and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine type drugs, and enhancement of alertness.
    Type: Grant
    Filed: July 24, 1990
    Date of Patent: March 10, 1992
    Assignee: Neurogen Corporation
    Inventor: Pamela Albaugh
  • Patent number: 5095115
    Abstract: An improved process for preparing riboflavin 5'-phosphate (FMN) or its monosodium salt by reacting riboflavin with excess phosphorus oxychloride in a solvent, hydrolyzing of the resulting reaction mixture and, if desired, partially neutralizing with aqueous sodium hydroxide solution, comprises reacting the riboflavin with from 1.2 to 3 moles of phosphorus oxychloride per mole of riboflavin in a suitable lactone, especially .gamma.-butyrolactone, as solvent. The process is particularly advantageous when the reaction mixture is hydrolyzed at from 80.degree. to 90.degree. C. continuously or batchwise.
    Type: Grant
    Filed: August 23, 1990
    Date of Patent: March 10, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Grimmer, Hans Kiefer
  • Patent number: 5086176
    Abstract: Adenosine analogues which act selectively at adenosine receptors and which act in general as adenosine antagonists are disclosed. From in vitro studies it is known that specific physiological effects can be distinguished as a result of this selectivity and that adenosine receptor activity in vitro correlates with adenosine receptor activity in vivo. Pharmaceutical preparations of the subject compounds can be prepared on the basis of the selective binding activity of the compounds disclosed herein which can be expected to enhance certain physiological effects while minimizing others, such as decreasing blood pressure without decreasing heart rate.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: February 4, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Norton P. Peet, Nelsen L. Lentz
  • Patent number: 5079249
    Abstract: The invention relates to compounds of formula I: ##STR1## in which m=2-4,n and p, which may be identical or different, are an integer equal to 1, 2 or 3, with the proviso that the sum of n and pq=0 or 1,R is a 1,2,3,4-tetrahydro-2,4-dioxo-3-quinazolinyl radical, optionally substituted, a 1,3,4,6,11,11a-hexahydro-1,3-dioxo-2H-pyrazino[1,2-b]isoquinol-2-yl radical, a 1,2-dihydro-1-oxo-2-phthalazinyl radical, optionally substituted, a 2,6-dioxo-1-piperazinyl radical of formula W: ##STR2## (R.sub.3 is a 2-pyridyl radical or an optionally substituted phenyl radical),a radical of formula Z: ##STR3## (R.sub.4 is a carbamoyl radical, a cyano radical, a hydroxycarbonyl radical or an alkoxycarbonyl radical having 1 to 6 carbon atoms),or a radical of formula Y: ##STR4## (R.sub.5 is a 2-pyrimidinyl radical, a 1-isoquinolyl radical, a 2-quinolyl radical, a 2-pyridyl radical, a benzyl radical, optionally substituted, a 2-thiazolyl radical, optionally substituted, or a 2-benzothiazolyl radical) andeither R.sub.1 and R.sub.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: January 7, 1992
    Assignee: Adir et Compagnie
    Inventors: Gilbert Lavielle, Francis Colpaert, Michel Laubie
  • Patent number: 5070086
    Abstract: Imidazo- and pyrimido-quinoline, naphthyridine and pyridopyrazine compounds, methods of making said compounds and their use as anti-allergy, antiinflammatory and/or agents for the treatment of hyperproliferative skin disease are disclosed.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: December 3, 1991
    Assignee: Schering Corporation
    Inventor: Richard Friary
  • Patent number: 5064826
    Abstract: This invention relates to novel triazolopyrimidine derivatives of formulae (Ia) and (Ib), ##STR1## wherein Q represents hydrogen, a heterocyclic group optionally substituted by a C.sub.1-4 alkyl group and containing one or more oxygen and/or nitrogen atoms or a group of formula--SR.sup.1 wherein R.sup.1 is alkyl or aralkyl, or a group of formula--NR.sup.2 R.sup.3 wherein R.sup.2 and R.sup.3 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl or a heterocyclic group,m and n are independently 0, 1, 2, 3 or 4, with the provision that if m stands for 0, then n is different from 0, and if both n and m are 1 or m stands for 0 and n is 2, the Q is different from methylthio or morpholino group, their mixtures or pharmaceutically acceptable salts. Furthermore, the invention relates to a process for preparing these compounds.The compounds of formulae (Ia) and (Ib) are able to inhibit the ptosis caused by tetrabenazine and they have analgetic activity.
    Type: Grant
    Filed: March 2, 1990
    Date of Patent: November 12, 1991
    Inventors: Klara Reiter nee Esses, Jozsef Reiter, Zoltan Budai, Endre Rivo, Peter Trinka, Lujza Petocz, Gabor Gigler, Istvan Gyertyan, Istvan Gacsalyi
  • Patent number: 5064947
    Abstract: Adenosine analogues which act selectively at adenosine receptors and which act in general as adenosine antagonists are disclosed. From in vitro studies it is known that specific physiological effects can be distinguished as a result of this selectivity and that adenosine receptor activity in vitro correlates with adenosine receptor activity in vivo. Pharmaceutical preparations of the subject compounds can be prepared on the basis of the selective binding activity of the compounds disclosed herein which can be expected to enhance certain physiological effects while minimizing others, such as decreasing blood pressure without decreasing heart rate.
    Type: Grant
    Filed: June 27, 1990
    Date of Patent: November 12, 1991
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Norton P. Peet, Nelsen L. Lentz
  • Patent number: 5032594
    Abstract: Novel tricyclic fused pyrimidine derivatives of the formula (I): ##STR1## wherein either one of R.sup.1 and R.sup.2 is hydrogen or an optionally substituted aralkyl group and the other is hydrogen, an optionally substituted aralkyl group or an aliphatic hydrocarbon group; R.sup.3 is hydrogen, an aliphatic hydrocarbon group or acyl group; and A is an optionally substituted divalent hydrocarbon chain having 2 to 4 carbon atoms and salts thereof are strong adenosine antagonists and activate cerebral functions and metabolisms, thus being useful as therapeutic or prophylactic agents for neurological or psychic changes caused by cerebral apoplexy, brain injury or cerebral atrophy.
    Type: Grant
    Filed: February 15, 1990
    Date of Patent: July 16, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Naka Takehiko, Nagaoka Akinobu
  • Patent number: 5017700
    Abstract: Riboflavin-4',5'-cyclophosphoric acid chloride of the formula I ##STR1## its preparation by reacting an alkali metal salt of riboflavin, in an aprotic solvent, with phosphorus oxychloride, its use for the preparation of riboflavin-5'-phosphate and of the sodium salt of riboflavin-5'-phosphate, and a process for the preparation of riboflavin-5'-phosphate or its sodium salt via the novel phosphoric acid ester chloride.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: May 21, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Grimmer, Hans Kiefer
  • Patent number: 5013737
    Abstract: Novel 2,4,8-trisubstituted-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5 (4H)-diones and 2,4,8-trisubstituted-4,5-dihydro-5-thioxo-3H, 6H-1,4,5a,8a-tetra-azaacenaphthylen-3-ones are disclosed which are useful antihypertensive and anxiolytic agents.
    Type: Grant
    Filed: February 21, 1990
    Date of Patent: May 7, 1991
    Assignee: American Cyanamid Company
    Inventors: Shin S. Tseng, Joseph W. Epstein, Jeremy I. Levin
  • Patent number: 5001148
    Abstract: Antihypercholesterolemic activity, due to competitive inhibition of HMG CoA reductase, has been found in compounds of the formula ##STR1## wherein: R.sup.1, R.sup.2 and R.sup.3 are independently selected from:(1) alkyl,(2) substituted alkyl in which one or more substituents are selected from(a) halogen,(b) hydroxyl,(c) alkoxy,(d) alkoxycarbonyl,(e) acyloxy,(f) cycloalkyl,(g) phenyl,(h) substituted phenyl in which one or more substituents are X or Y,(i) alkyl-S(O).sub.n,(j) cycloalkyl-S(O).sub.n,(k) phenyl-S(O).sub.n,(l) substituted phenyl-S(O).sub.n in which one or more substituents are X or Y, and(m) oxo,(3) alkoxy,(4) alkenyl,(5) cycloalkyl,(6) substituted cycloalkyl in which one or more substituents are selected from(a) alkyl,(b) substituted alkyl in which one or more substituents are selected from(i) halogen,(ii) hydroxy,(iii) alkoxy,(iv) alkoxycarbonyl(v) acyloxy(vi) phenyl(vii) substituted phenyl in which one or more substituents are X and Y,(viii) alkyl-S(O).sub.n,(ix) cycloalkyl-S(O).sub.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: March 19, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jeffrey O. Saunders, Eric M. Gordon
  • Patent number: 4992442
    Abstract: Pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidine derivatives are disclosed. The compounds are represented by the formula (I), ##STR1## wherein R.sub.1 and R.sub.2 individually represent a hydrogen atom, a linear or branched alkyl group which may have a substituent, a cycloalkyl or phenyl group which may have a substituent, or a heterocyclic group which may have a substituent, and R.sub.3 is a hydrogen atom or a cyano group. The compounds have excellent circulatory disease curing activities as well as bronchodilation activities.
    Type: Grant
    Filed: October 3, 1989
    Date of Patent: February 12, 1991
    Assignee: Pola Chemical Industries Inc., Japan
    Inventors: Michihiko Tsujitani, Kenichi Kishii, Masato Inazu, Toshihiro Morimoto, Yoshiaki Motoki, Ichiro Matsuo
  • Patent number: 4977190
    Abstract: Riboflavin produced by a microbial method is prepared in the form of free-flowing, non-dusting, spray-dried granules or microgranules as a feed additive by removing water from the mixture discharged from microbial fermentation for the preparation of riboflavin, wherein the mixture is subjected to(a) a fluidized-bed spray-drying process(b) a one-material spray-drying process or(c) a disk spray-drying process without significant amounts of binders being added to the discharged fermentation mixture.
    Type: Grant
    Filed: June 9, 1989
    Date of Patent: December 11, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Meyer, Wolfgang Buehler, Johannes Grimmer, Gunter Eipper, Hans Kiefer, Christoph Martin
  • Patent number: 4968690
    Abstract: The new compound 3-deazaneplanocin A has been discovered to have potent anti-viral, anti-tumor activity and differentiating activity. A simple method for preparing 3-deazaneplanocin A has been developed involving nucleophilic substitution, which method can also be used to prepare a great variety of carbocyclic nucleosides.
    Type: Grant
    Filed: January 19, 1989
    Date of Patent: November 6, 1990
    Assignee: United States Government as represented by the Secretary of the Dept. of Health and Human Services
    Inventors: Victor E. Marquez, John S. Driscoll, Mu-Ill Lim, Christopher K. Tseng, Alberto Haces, Robert I. Glazer
  • Patent number: 4968797
    Abstract: 4,4-diaryldihydroquinazolones of the formula ##STR1## wherein X.sup.1, X.sup.2 and X.sup.3, independently of one another, denote hydrogen, halogen, alkyl, aryl, alkanoylamino, aroylamino, heteryl, NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3, at least one of the radicalsX.sup.1, X.sup.2 or X.sup.3 standing for NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3,R.sup.1 denotes hydrogen, alkyl, cycloalkyl, aralkyl, aryl or the members of a bridge to the o-carbon of ring C,R.sup.2 denotes a radical of an acid,Y.sup.1, Y.sup.2 and Y.sup.3, independently of one another, denote hydrogen, alkyl, cycloalkyl, aralkyl aryl or heteryl or the remaining members of a 5- or 6-membered ring which reaches to one of the o-position benzene C atoms and may contain further hetero atoms orY.sup.1 +Y.sup.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: November 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Berneth, Alfred Brack, Karlheinrich Meisel
  • Patent number: 4954498
    Abstract: The present invention provides tricyclic benzimidazoles of the formula: ##STR1## wherein R.sub.1 is a phenyl radical of the general formula: ##STR2## wherein R.sub.2, R.sub.3 and R.sub.4 can be the same or diferent as in claim 1. For A, B, C and D are understood those compounds where one or two of A, B, C or D are nitrogen. These compounds are useful to inhibit the aggregation of thrombocytes and erythrocytes, lower blood pressure and can increase the power of the heart.
    Type: Grant
    Filed: January 15, 1988
    Date of Patent: September 4, 1990
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Wolfgang von der Saal, Erwin Boehm, Klaus Strein
  • Patent number: 4925939
    Abstract: The present invention concerns compounds of the formula: ##STR1## wherein R is a lower alkyl group, an aryl group or an alkylaryl group and X and Y are the same or different, and each is OH, NH.sub.2, or SH. The aryl group or the aryl moiety of the alkylaryl group may be unsubstituted, monosubstituted, disubstituted or trisubstituted. If substituted, each substituent may independently be an alkyl group, an alkyloxy group or a halogen.The present invention also provides methods for synthesizing the compounds described above.
    Type: Grant
    Filed: January 5, 1989
    Date of Patent: May 15, 1990
    Assignee: Sloan-Kettering Institute for Cancer Research
    Inventor: Kyoichi A. Watanabe
  • Patent number: 4916137
    Abstract: This disclosure described novel 5-(substituted-amino)-8-(substituted-phenyl)-3H,6H, -1,-4,5a,8a-tetraazaacenaphthylen-3-ones useful for the treatment of cognitive and related neural behavioral disorders in mammals.
    Type: Grant
    Filed: November 30, 1988
    Date of Patent: April 10, 1990
    Assignee: American Cyanamid Company
    Inventors: Joseph W. Epstein, Jeremy I. Levin, Shin S. Tseng
  • Patent number: 4912104
    Abstract: Novel tricyclic fused pyrimidine derivatives represented by the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently C.sub.1-8 alkyl or C.sub.2-8 alkenyl;R.sup.3 is hydrogen, C.sub.1-3 alkyl, C.sub.2-3 alkenyl, C.sub.1-6 alkyl-CO-, optionally substituted benzoyl, C.sub.1-4 alkyl-O-CO-, carbamoyl or formyl; andA is C.sub.2-4 alkylene or C.sub.2-4 alkenylene which may be substituted with C.sub.1-3 alkyl, halogen, nitro, amino, oxo, or phenyl optionally substituted with 1 to 2 members selected from the class consisting of amino, nitro, hydroxy, methoxy and methyl, and a salt thereofare useful for antiinflammatory, analgesic, antipyretic, anti-allergic anti-psoriatic and liver-protecting agent.
    Type: Grant
    Filed: August 16, 1988
    Date of Patent: March 27, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takehiko Naka, Taketoshi Saijo, Hiroshi Satoh
  • Patent number: 4904658
    Abstract: Substituted-6H,8H-pyrimido[1,2,3-cd]purine-8,10(9H)-diones and substituted-6H,10H-pyrimido[1,2-cd]purin-10-ones which are useful as cognition enhancing agents, anxiolytic agents and/or antihypertensive agents in the treatment of cognitive and relative neutral behavioral problems, anxiety and hypertension in mammals.
    Type: Grant
    Filed: April 15, 1988
    Date of Patent: February 27, 1990
    Assignee: American Cyanamid Company
    Inventors: Shin S. Tseng, Joseph W. Epstein, Jeremy I. Levin
  • Patent number: 4902686
    Abstract: New heterocyclic compounds having the general formula ##STR1## wherein R.sup.3 is ##STR2## CO.sub.2 R' or CONR'R", wherein R' and R" independently are C.sub.1-6 -alkyl, C.sub.3-7 -cycloalkyl or C.sub.1-6 -alkoxymethyl;--A-- is --C(.dbd.O)--NR'"--, --NR'"--C(.dbd.O)--, or ##STR3## wherein R'" is C.sub.1-6 -alkyl; X is C or N; andR.sup.4 is hydrogen, halogen, CN, C.sub.1-6 -alkyl, C.sub.1-6 -alkynyl, trimethylsilyl-C.sub.1-6 -alkynyl, aryloxy which may be substituted with halogen, aralkoxy, C.sub.3-7 -cycloalkoxy which may be substituted with one or more C.sub.1-6 -alkyl groups, or NR""R'"", wherein R"" and R""' independently are C.sub.1-6 -alkyl or together with the nitrogen atom form a 3-7 membered heterocyclic ring.The compounds are useful in psychopharmaceutical preparations as anticonvulsants, anxiolytics, hypnotics, and nootropics.
    Type: Grant
    Filed: April 20, 1989
    Date of Patent: February 20, 1990
    Assignee: A/S Ferrosan
    Inventors: Frank Watjen, Holger C. Hansen
  • Patent number: 4902604
    Abstract: Photopolymerizable initiator compositions having high photosensitivity to light sources giving visible rays and the other rays in the longer wavelengths. The compositions containing polymerizable compounds having ethylenic unsaturated bonds and salts formed by an organic boron compound anion and an organic cationic azulene dye compound comprising an azulene ring having a nitrogen atom or a chalcogen atom in the 2- or 4- position can be used for making lithographic printing plates, resinous relief printing plates, and resists or photomasks for printed circuit substrates.The polymerizable compounds having ethylenic unsaturated bonds can be encapsulated to obtain microcapsules to be used for the formation of black-and-white or color images.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: February 20, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Jun Yamaguchi, Masaki Okazaki, Takanori Hioki
  • Patent number: 4900819
    Abstract: The disclosure relates to a method of initiating a crystal growth prior to filtering off, from the mother liquor in which they were produced, of such crystalline explosives of the type hexogen and octogen produced by the so-called Bachmann process or variations of this process.According to the invention, the mother liquor is, after the end of the chemical reaction proper, subjected to a pressure-heat treatment which initiates the partial dissolution of the crystalline explosives obtained in the process, giving rise, after cooling of the mother liquor, to larger crystals which may more readily be filtered off.According to a further improvement of the invention a relatively pure octogen may be extracted from the mother liquor by way of a thermo-filtering of said liquor at a temperature of 60.degree.-110.degree. C.
    Type: Grant
    Filed: April 21, 1988
    Date of Patent: February 13, 1990
    Assignee: Nobel Kemi AB
    Inventors: Per Ericsson, Leif Svensson, Nils-Ingvar Olsson, Bertil Bergstrom
  • Patent number: 4898943
    Abstract: Novel tricyclic triazolopyrimidine compounds represented by formula (I) shown in the specification and physiologically acceptable salts thereof are disclosed. These compounds have an excellent anti-allergic activity and are useful for treatment and prophylaxis of allergic diseases.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: February 6, 1990
    Assignee: Daiichi Seiyaku Co., Ltd.
    Inventors: Sumiro Isoda, Shunzo Aibara, Tamotsu Miwa, Hiroyuki Fujiwara, Shuichi Yokohama, Hiroo Matsumoto
  • Patent number: 4873244
    Abstract: New heterocyclic compounds having the general formula ##STR1## wherein ##STR2## CO.sub.2 R' or CONR'R", whereinR' and R" independently are C.sub.1-6 -alkyl, C.sub.3-7 -cycloalkyl or C.sub.1-6 -alkoxymethyl;--A-- is --C(.dbd.O)--NR'"--, --NR'"--C(.dbd.O)--, or ##STR3## wherein R'" is C.sub.1-6 -alkyl;X is C or N; andR.sup.4 is hydrogen, halogen, CN, C.sub.1-6 -alkyl, C.sub.1-6 -alkynyl, trimethylsilyl-C.sub.1-6 -alkynyl, aryloxy which may be substituted with halogen, aralkoxy, C.sub.3-7 -cycloalkoxy which may be substituted with one or more C.sub.1-6 -alkyl groups, or NR""R'"", wherein R"" and R'"" independently are C.sub.1-6 -alkoxy or together with the nitrogen atom form a 3-7 membered heterocyclic ring.The compounds are useful in psychopharmaceutical preparations as anticonvulsants, anxiolytics, hypnotics, and nootropics.
    Type: Grant
    Filed: February 16, 1988
    Date of Patent: October 10, 1989
    Assignee: A/S Ferrosan
    Inventors: WaFrank, Holger C. Hansen
  • Patent number: 4871732
    Abstract: The present invention is directed to a group of compounds which are imidazo[2,1-b]quinazolin-5(3H)-ones, related tricyclic compounds, and pharmaceutically acceptable salts thereof. These compounds are useful as bronchodilators. These compounds are prepared by the reaction of an appropriate hydrazine with an appropriate 1-substituted-2-methyl-2-imidazoline or chemically equivalent compound.
    Type: Grant
    Filed: September 22, 1988
    Date of Patent: October 3, 1989
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Norton P. Peet, Shyam Sunder
  • Patent number: 4859774
    Abstract: The flowability of stored triethylenediamine is improved by admixing with a flow promoting amount of a salt, amide or ester derivative of a C.sub.8 -C.sub.22 fatty acid. Especially suitable flow promoting additives for triethylenediamine are sales of stearic acid.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: August 22, 1989
    Assignee: Air Products and Chemicals Inc.
    Inventors: Akio Takahashi, Robert G. Petrella, Joel Schwartz
  • Patent number: 4847377
    Abstract: Substituted 2,3-dihydro-6-substituted-pyrimido[2,1-f]purine-4,8(1H, 9H)-diones, their tautomers and salts, are disclosed for use as antihyperproliferative skin disease agents.Methods for their preparation and use are described.
    Type: Grant
    Filed: October 8, 1987
    Date of Patent: July 11, 1989
    Assignee: Schering Corporation
    Inventors: Daniel M. Solomon, James J. Kaminski, David J. Conn
  • Patent number: 4838925
    Abstract: This invention relates to novel heterocyclic carbonyl sulfonamides which are particularly useful as agricultural chemicals.
    Type: Grant
    Filed: September 25, 1987
    Date of Patent: June 13, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Chi-Ping Tseng
  • Patent number: 4831013
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is optionally substituted phenyl, pyridyl, thienyl, furyl, pyrrolyl, thiazolyl, or ribofuranosyl; X is oxygen, NR, or sulfur; R is hydrogen, lower alkyl, lower alkenyl, or lower alkynyl; and ring A is (a) an optionally substituted 5-8 membered monocycloalken-1,2-diyl; (b) an optionally substituted carbobicyclic ring of the formula ##STR2## wherein n and m are each independently one or two; or (c) an optionally substituted 5-6 membered heterocycle having one or two heteroatoms, the atoms of which are selected from carbon, oxygen, nitrogen, and sulfur. Also disclosed are tautomers of the above and pharmaceutically acceptable salts; compositions thereof; and methods of using the compounds, tautomer, or salts.
    Type: Grant
    Filed: February 27, 1987
    Date of Patent: May 16, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: John E. Francis
  • Patent number: 4831029
    Abstract: The invention relates to condensed cyclic triazole derivatives of the general Formula I ##STR1## and pharmaceutically acceptable salts thereof. The compounds of the general Formula I possess useful sedative and tranquillant properties and exhibit particularly spasmolytic, motility inhibiting, and narcosis potentiating, yohimbine potentiating and local anaesthetic and also weak reserpine ptosis inhibiting effect.
    Type: Grant
    Filed: November 5, 1987
    Date of Patent: May 16, 1989
    Inventors: Jozsef Reiter, Endre Rivo, Klara Reiter nee Esess, Marton Fekete, Frigyes Gogenyi, Lujza Petocz, Istvan Gacsalyi, Istvan Gyertyan
  • Patent number: 4826981
    Abstract: There is disclosed a process for preparing 9-(2-hydroxyethoxymethyl)-guanine (acyclovir) of the formula IV ##STR1## wherein a novel compound of the formula I ##STR2## wherein R and R' may be the same or different and represent hydrogen, (C.sub.1 -C.sub.8)acyl or benzyl and R.sub.1 represents (C.sub.1 -C.sub.8)acyl, is hydrolyzed basic conditions. Also disclosed is the novel compound of the formula I, a process for the preparation thereof by condensing a novel compound of the formula II ##STR3## with a compound A--CH.sub.2 --O--CH.sub.2 CH.sub.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: May 2, 1989
    Assignee: KRKA
    Inventors: Joze Kobe, Joze Gnidovec, Pavle Zupet
  • Patent number: 4816458
    Abstract: Substituted 2,3-dihydro-6-substituted-pyrimido[2,1-f]purine-4,8(1H,9H)-diones, their tautomers and salts, are disclosed for use as antihyperproliferative skin disease agents.Methods for their preparation and use are described.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: March 28, 1989
    Assignee: Schering Corporation
    Inventors: Daniel M. Solomon, James J. Kaminski
  • Patent number: 4806643
    Abstract: Riboflavin of the formula I ##STR1## is prepared by an improved process by condensing a 4,5-dimethyl-N-(D)-ribityl-2-phenylazoaniline of the formula II ##STR2## where R is H, --CL, --NO.sub.2, --CH.sub.3 or --OCH.sub.3 in the o- or p-position, with barbituric acid of the formula III ##STR3## in the presence of an acid as a condensing agent, by a process in which the acidic condensing agent used is an aliphatic secondary carboxylic acid of the general formula IV ##STR4## where R.sup.1 is methyl or ethyl and R.sup.2 is alkyl of 3 or 4 carbon atoms.
    Type: Grant
    Filed: November 19, 1986
    Date of Patent: February 21, 1989
    Assignee: BASF Aktiengesellschaft
    Inventor: Johannes Grimmer
  • Patent number: 4778511
    Abstract: Novel fluorine-containing N-sulfenylated indazoles are prepared by reacting the corresponding indazoles with sulfenyl halides in the presence of a solvent and/or diluent and in the presence of an acid-binder. The novel fluorine-containing N-sulfenylated indazoles are useful in the protection of industrial materials against attack by microorganisms such as bacteria, fungi, yeast, algae, and slime as plant protection agents, and in combating insects and arachrids.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: October 18, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Heywang, Bernd Baasner, Albrecht Marhold, Wilfried Paulus, Paul Reinecke, Hans-Georg Schmitt
  • Patent number: 4754034
    Abstract: 4,4-diaryldihydroquinazolones of the formula ##STR1## wherein X.sup.1, X.sup.2 and X.sup.3, independently of one another, denote hydrogen, halogen, alkyl, aryl, alkanoylamino, aroylamino, heteryl, NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3, at least one of the radicals X.sup.1, X.sup.2 or X.sup.3 standing for NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3,R.sup.1 denotes hydrogen, alkyl, cycloalkyl, aralkyl, aryl or the members of a bridge to the o-carbon of ring C,R.sup.2 denotes a radical of an acid,Y.sup.1, Y.sup.2 and Y.sup.3, independently of one another, denote hydrogen, alkyl, cycloalkyl, aralkyl aryl or heteryl or the remaining members of a 5- or 6-membered ring which reaches to one of the o-position benzene C atoms and may contain further hetero atoms orY.sup.1 +Y.sup.
    Type: Grant
    Filed: October 21, 1985
    Date of Patent: June 28, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Berneth, Alfred Brack, Karlheinrich Meisel
  • Patent number: 4725596
    Abstract: Certain pyrimidine derivatives are useful in treating allergic, inflammatory and hyperproliferative skin diseases and in suppressing the immune response. Methods for preparing the compounds and methods for their use are also described.
    Type: Grant
    Filed: August 15, 1986
    Date of Patent: February 16, 1988
    Assignee: Schering Corporation
    Inventors: Richard J. Friary, Sidney R. Smith, Marvin I. Siegel
  • Patent number: 4716161
    Abstract: A phenylpiperazine derivative according to the present invention has the following general formula [I]: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen or alkoxy group having 1 to 3 carbon atoms, orR.sup.1 and R.sup.2 or R.sup.2 and R.sup.3 together with carbon atoms to which they are attached form --O(CH.sub.2).sub.m O-- wherein m is an integer of 1 to 3, oreither R.sup.1 or R.sup.2 is amine residue selected from the group consisting of --NH.sub.2 , --NHSO.sub.2 CH.sub.3, --NHCOCH.sub.3 and --NHCONH.sub.2 and the other is hydrogen or alkoxy group of 1 to 3 carbon atoms and R.sup.3 is hydrogen;R.sup.4 and R.sup.5 are independently hydrogen or alkyl group of 1 to 3 carbon atoms;Y is --CO-- or --SO.sub.2 -- provided that at least one of R.sup.1 and R.sup.2 is not hydrogen when Y is --CO--; andn is an integer of 2 to 4.An acid addition salt of the phenylpiperazine derivative having the general formula [I] is included in the present invention.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: December 29, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Harukazu Fukami, Ryoji Kikumoto, Kenichiro Nakao, Issei Nitta, Shinya Inoue