Ring Nitrogen Is Shared By The Cyclos Of The Bicyclo Ring System (e.g., Tetramisole, Etc.) Patents (Class 514/368)
  • Patent number: 5468765
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: November 21, 1995
    Assignee: Pfizer Inc.
    Inventors: Bernard J. Banks, Christopher J. Dutton, Alexander C. Goudie
  • Patent number: 5459147
    Abstract: The invention relates to substituted benzimidazolyl derivatives of the general formula ##STR1## wherein A and R.sub.a to R.sub.c are defined as in claim 1, the mixtures of position isomers thereof and the salts thereof which have valuable properties.These compounds have valuable pharmacological properties, particularly angiotensin-antagonistic effects and preferably angiotensin-II-antagonistic effects.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: October 17, 1995
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Norbert Hauel, Uwe Ries, Berthold Narr, Jacques van Meel, Wolfgang Wienen, Michael Entzeroth
  • Patent number: 5384325
    Abstract: Compounds based on heterobicyclic derivatives displaying fungicidal activity, having the general formula (I): ##STR1##
    Type: Grant
    Filed: April 25, 1994
    Date of Patent: January 24, 1995
    Assignee: Isagro S.r.l.
    Inventors: Giovanni Camaggi, Lucio Filippini, Marilena Gusmeroli, Raul Riva, Carlo Garavaglia, Ernesto Signorini, Mario Ferri
  • Patent number: 5212192
    Abstract: The present invention relates to novel 6-aryl-5,6-dihydroimidazo[2,1-b]thiazole derivatives having immunostimulating properties, which are useful for treating humans and warm-blooded animals suffering from disorders and/or diseases wherein the immune system is impaired or suppressed. Processes of preparing said novel compounds and compositions containing the same as active ingredient.
    Type: Grant
    Filed: December 19, 1991
    Date of Patent: May 18, 1993
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Alfons H. M. Raeymaekers, Leopold F. C. Roevens, Willy J. C. Van Laerhoven, Jean P. F. Van Wauwe
  • Patent number: 5135847
    Abstract: A composition contains levamisole and a substrate for alkaline phosphatase in a high pH buffer including 2-amino-2-methyl-1-propanol. The composition may be included in a kit of materials useful in performing an immunoassay in which intestinal alkaline phosphatase is the label. The invention includes a method for detection of a viral antigen by an immunoassay including intestinal alkaline phosphatase as the label and the composition of the invention to provide stabilized levamisole to inhibit nonintestinal alkaline phosphatase.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: August 4, 1992
    Assignee: Becton, Dickinson and Company
    Inventor: Randal A. Hoke
  • Patent number: 5134150
    Abstract: A method of inhibiting the 5-lipoxygenase pathway in an animal in need thereof which comprises administering an effective, 5-lipoxygenase pathway inhibiting amount of a diaryl- substituted imidazole fused to a thiazole pyrrolidine, thiazide or piperidine ring to such animal.
    Type: Grant
    Filed: December 4, 1989
    Date of Patent: July 28, 1992
    Assignee: SmithKline Beecham Corporation
    Inventors: Paul E. Bender, John G. Gleason, Don E. Griswold, Nabil Hanna, Ivan Lantos, Kazys A. Razgaitis, Henry M. Sarau, Susan C. Shilcrat
  • Patent number: 5116954
    Abstract: Substituted six-membered benzo-fused heterocycles of the formula (I) ##STR1## in which: X=0, NH, S.fwdarw.(O).sub.n (n=0 or 2);R.sub.1 is phenyl, phenyl substituted by methoxy, hydroxy, chlorine, fluorine, diethylaminoethoxy, phenoxy, 2-methyl-4-thiazolyl, 2-amino-4-thiazolyl, phenyl, amino, nitro, terbutyl, carboxymethyl, acetamido, dimethyltriazenyl, benzoyl, hexyl, undecyl, trifluoromethyl, carbamoyl; or R.sub.1 is trifluoromethyl, pyridyl-2,pyridyl-4;R.sub.2 is H, methoxy, hydroxy; orR.sub.1 and R.sub.2 are --CH.dbd.CH--CH.dbd.CH--;R.sub.3 and R.sub.4 are methoxy, hydroxy, fluorine or form a fused benzene ring;CR.sub.5 R.sub.6 R.sub.7 is carboxymethyl, --CH.sub.2 --PO.sub.3 H,--CH.sub.2 --PO(oET).sub.2, 4-methylpiperazinyl, aminomethyl,3-4-5-trimethoxyphenylaminomethyl, acetyl, bromoacetyl, hydroxyethyl, acetoxyethyl, mercaptomethyl, acetylthiomethyl, methoxy-carbopnylthiomethyl, --CH--CONH.sub.2, ##STR2## substituted thiazolyl, subsituted furanone, imidazo(1,2-a)pyridinyl, indolizinyl, or R.sub.4 and R.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: May 26, 1992
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Philippe Briet, Jean-Jacques Berthelon, Francois Collonges
  • Patent number: 5116836
    Abstract: Novel 3-aryl-pyrrolidine 2,4-dione derivatives of the formula ##STR1## having pesticidal activity.
    Type: Grant
    Filed: August 15, 1990
    Date of Patent: May 26, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reiner Fischer, Hermann Hagemann, Andreas Krebs, Albrecht Marhold, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen, Benedikt Becker, Wilhelm Stendel, Christoph Erdelen
  • Patent number: 5098919
    Abstract: A compound represented by the following formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom, an alkyl group or a cyclic alkyl group;R.sub.2 represents a hydroxyl group, an alkoxy group which may have one to three substituents in the alkyl group moiety, an arylthio group which may have one or more substituents in the aryl group moiety, an aryloxy group which may have one or more substituents in the aryl group moiety, an amino group, an alkylamino group or a cyclic amino group which may contain other hetero atoms as ring atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom;R.sub.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: March 24, 1992
    Assignee: Daiichi Pharmaceutical Co., Ltd.
    Inventors: Norio Suzuki, Atsushi Nakayama, Toru Hosokami, Masashi Hasegawa, Shuichi Yokohama
  • Patent number: 5036082
    Abstract: Nitro-substituted heterocyclic compounds of the formula (I) ##STR1## wherein R is hydrogen or alkyl, Z is an optionally substituted aryl or optionally substituted heterocyclic group containing at least one atom selected from N, O and S,A is optionally substituted ethylene or optionally substituted trimethylene, andB stands for 2 or 3 members of a heterocyclic ring which is formed, together with the adjacent C-atom and N-atom and at least one of said members may represent a hetero atom and may be optionally substituted, provided that when B stands for 3 members, two of which are carbon atoms and the other one is a nitrogen atom which is located in the middle of the three members, then at least one of said two carbon atoms must be substituted by a keto group. Such compounds being useful as insecticides.
    Type: Grant
    Filed: April 18, 1990
    Date of Patent: July 30, 1991
    Assignee: Nihon Tokushu Noyaku Seizo K. K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shoko Sasaki, Koichi Moriya, Yumi Hattori, Katsuhiko Shibuya
  • Patent number: 4952594
    Abstract: The administration internally to humans of certain imidazol derivatives, especially 1-(Beta-hydroxyethyl)-2-methyl-5-nitro-imidazole (metgronidazole); N"-cyano-N-methyl-N'-[2[[(5-methyl-1H-imidazol-4-yl) methyl]thio]ethyl]-guanidine (cimetidine); 6-[1-methyl-4-nitro-imidazol-5-yl)thio] purine (azathioprine); L-(-)-2,3,5,6-Tetrahydro-6-phenyl-imidazo[2,1-b]thiazole (levamisole), or salts of the above compounds, is an effective therapeutic treatment for multiple sclerosis, both acute and chronic. The imidazole moeity is theorized to directly inhibit spread of the virus theorized to cause multiple sclerosis. Treatment of multiple sclerosis with metronidazole with one bolus dose on a frequency of once a day or less and with cimetidine on a frequency of twice per day has been found to be highly efficatious with minimal suppression of the patient's natural immune system and minimal long term peripheral nerve damage.
    Type: Grant
    Filed: June 14, 1988
    Date of Patent: August 28, 1990
    Inventor: James B. Mercer
  • Patent number: 4880824
    Abstract: Heterocyclic compounds of formulae (I) and (II): ##STR1## where R.sup.1 and R.sup.2 are alkyl, R.sup.3 is H or alkyl, m is 2-5 and Het is a hetercycle such as thiazole, benzothiazole, substituted benzothiazole, pyrazine, triazine, thiadiazole, substituted thiadiazole, pyrimidine or substituted pyrimidine. The compounds are calcium channel blockers useful in the treatment of cardiovascular conditions such as hypertension or angina.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: November 14, 1989
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Jeffery B. Press, Maud Urbanski
  • Patent number: 4879293
    Abstract: The compound of the formula ##STR1## wherein X is a cyclic group which may optionally be substituted; Y is a carboxyl group which may optionally be esterified or amidated; Z is --CH.dbd.CH--CH.dbd.CH--, --S--(CH.sub.2).sub.l --S-- is an integer of 1 to 3), --N.dbd.CH--CH.dbd.N-- or --(CH.sub.2).sub.m --(m is an integer of 3 to 5); ring A may optionally be substituted with halogen, nitro, amino, alkanoylamino, alkoxycarbonyl, carboxyl or carbamoyl; and n is an integer of 1 to 3, and salts thereof. The compounds display a strong antianxiety effect to mammalian animals and are useful for the prevention or treatment of a disease such as psychoromatic disease and anxiety neurosis.
    Type: Grant
    Filed: September 8, 1988
    Date of Patent: November 7, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kentaro Hiraga, Yoshiaki Saji
  • Patent number: 4857539
    Abstract: Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms;Z is N or HC;R is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when Z is N, R is lower-alkyl;R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; andHet is selected from specified heterocyclic groups,are useful and antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: August 15, 1989
    Assignee: Sterling Drug Inc.
    Inventors: Guy D. Diana, Philip M. Carabateas
  • Patent number: 4853402
    Abstract: By using .alpha.-mimetics, particularly compounds of general formulae I to III and the compounds listed in Table I, as feed additives in fattening animals, it has surprisingly been possible to improve the daily weight gain, the utilisation of fodder and the ratio of muscle to fat in favor of the proportion of muscle and protein.
    Type: Grant
    Filed: February 26, 1987
    Date of Patent: August 1, 1989
    Assignee: Boehringer Ingelheim Vetmedica GmbH
    Inventors: Werner Bomann, Franz Esser, Ulrich Hamel, Helmut Stable
  • Patent number: 4794120
    Abstract: Nitrofuran derivatives of formula (I) ##STR1## in which n is 0 or 1 and R is a selected heterocyclic radical have useful antibacterial, antiparasitic and antifungal activity.
    Type: Grant
    Filed: July 7, 1987
    Date of Patent: December 27, 1988
    Assignee: Synthelabo
    Inventors: Philippe Manoury, Jean Binet, Michel Aletru
  • Patent number: 4735957
    Abstract: New thiazole derivatives of the formula: ##STR1## wherein R.sup.1 is lower alkyl, carboxy, a drivative of carboxy, hydroxymethyl, halomethyl, lower alkylthiomethyl, hydroxyiminomethyl or alkenyl which may be substituted with lower alkoxycarbonyl, pyridyl or cyano,R.sup.2 is hydrogen, hydroxy, lower alkyl, pyridyl, amino, lower alkylamino, pyridylamino, arylamino, acylamino, N-(lower)alkylN-acylamino, guanidino optionally substituted with dimethylaminomethylene, or ar(lower)alkylamino optionally substituted with lower alkoxy,R.sup.3 is lower alkyl, halo(lower)alkyl or N-containing unsaturated heterocyclic group which may be substituted with halogen, lower alkyl, lower alkoxy, carboxy, a derivative of carboxy, hydroxy, pyridyl, amino, lower alkylamino, pyridylamino, arylamino, acylamino, N-(lower)alkyl-N-acylamino, guanidino, N-oxide or ar(lower)alkylamino optionally substituted with lower alkoxy,Q is --CO--, andn is an integer of 0 or 1,provided that when both of R.sup.1 and R.sup.
    Type: Grant
    Filed: November 18, 1986
    Date of Patent: April 5, 1988
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takao Takaya, Hisashi Takasugi
  • Patent number: 4684658
    Abstract: The invention provides novel pyrrole derivatives of formula: ##STR1## in which R'=H, alkyl or phenyl optionally substituted by halogen, alkyl, alkyloxy or alkylthio, Z=0 or S, p=0 or 1, andeither A is a heterocyclic ring such that it forms, with pyrrole, a 1H,3H-pyrrolo[1,2-c]thiazole, 2,3-dihydro-1H-pyrrolizine optionally substituted by OH, 5,6,7,8-tetrahydroindolizine, 1,2-dihydro-4H-pyrrolo[1,2-c]-1,3-thiazine, 2,3-dihydropyrrolo[2,1-b]thiazole, 1H,3H-pyrrolo[1,2-c]oxazole, 1,2-dihydro-4H-pyrrolo]1,2-c]-1,3-oxazine or 2,3-dihydropyrrolo[2,1-b]oxazole ring system, n=0 or 1, Het=3-pyridyl or 5-thiazolyl, and(1) either R=H, halogen, alkyl or phenyl optionally substituted by halogen, alkyloxy or alkylthio and Y=alkyl or phenyl optionally substituted by halogen, alkyl, alkyloxy or alkylthio, or Y=--NR.sub.1 R.sub.2 with:either R.sub.1 =H and R.sub.2 =unsubstituted alkyl, cycloalkyl (C.sub.3 -C.sub.6), alkenyl (C.sub.2 -C.sub.4), alkynyl (C.sub.3 -C.sub.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: August 4, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Louis Fabre, Daniel Farge, Claude James, Daniel Lave
  • Patent number: 4672072
    Abstract: A pour-on formulation which allows the simultaneous control of internal and external parasites in mammals by a single localized superficial application comprises a pyrethroid in admixture with a thiazole or salt or ester thereof.
    Type: Grant
    Filed: March 13, 1985
    Date of Patent: June 9, 1987
    Assignee: Wellcome Australia Limited
    Inventors: Ronald J. Hackney, James J. Guinan
  • Patent number: 4657920
    Abstract: 1,2,4-Triazol-1-yl-methyl-carbinols of the formula ##STR1## in which Ar is optionally substituted aryl, andHet is optionally substituted heteroaryl with at least 2 different hetero-atoms,or addition products thereof with plant-tolerated acids or metal salts, which possess fungicidal activity.
    Type: Grant
    Filed: March 22, 1985
    Date of Patent: April 14, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jan Gajowski, Erik Regel, Karl H. Buchel, Wilhelm Brandes, Paul Reinecke
  • Patent number: 4618618
    Abstract: The invention concerns novel compounds selected from D,L-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]-thiazolium 4-cyano-2-iodo-6-nitrophenoxide and L-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazolium 4-cyano-2-iodo-6-nitrophenoxide. The compounds are anthelmintics effective against both nematodes and trematodes and in further embodiments the invention provides processes for the preparation of the compounds of the invention, compositions comprising as active ingredient the compounds of the invention and processes for killing helminths using the compounds of the invention.
    Type: Grant
    Filed: December 28, 1984
    Date of Patent: October 21, 1986
    Inventor: Errol J. McGarry
  • Patent number: 4600583
    Abstract: The method of improving the storage stability of parenterally administerable physiologically active compositions which comprises, incorporating in said compositions a small but effective amount of a compound of the formulae, ##STR1## wherein R is H, lower alkyl or acyl; each R.sup.1 is H or lower alkyl; and n is an integer of from 1 to 6; x is 0 or 1; each Y is H; and the non-toxic pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: September 7, 1982
    Date of Patent: July 15, 1986
    Assignee: Tetra Consultants Inc.
    Inventors: Erik Stevens, Ernestina M. Van Hoeyveld
  • Patent number: 4600582
    Abstract: A method of reducing local adverse reactions which occur at the site of administration of parenterally administrable physiologically active compositions, to patients which comprises, prior to administration thereof, incorporating in said physiologically active compositions, a small but effective amount of a compound of the formulae, ##STR1## wherein n is an integer of from 1 to 6; R.sup.1 is H or lower alkyl; x is 0 or 1; each Y is H; and R is H, lower alkyl or acyl; and the non-toxic pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: September 7, 1982
    Date of Patent: July 15, 1986
    Assignee: Tetra Consultants, Inc.
    Inventors: Erik Stevens, Ernestina M. Van Hoeyveld
  • Patent number: 4584305
    Abstract: Process of aiding regression and palliation of neoplastic disease in animal and human hosts comprising systemic administration to phenylimidazo[2,1-b]thiazole or a nontoxic acid addition salt thereof. Preferably the active ingredient is administered in a sufficient amount to provide dosages over the range from about 1 mg to about 5 mg/kg of body weight of the host.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: April 22, 1986
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Josephus Brugmans, William Pollack, Paul A. J. Janssen, Daniel Tripodi
  • Patent number: 4557932
    Abstract: The present invention relates to a new compounded composition with synergistic properties, to dosage units thereof, and to the use of the said compounded composition and dosage units.The composition contains as active ingredients the amidinopenicillanic acid mecillinam or a pharmaceutically acceptable, non-toxic salt or pro-drug thereof in combination with another antibiotic compound of the formula ##STR1## or a pharmaceutically acceptable, non-toxic salt or pro-drug thereof, optionally together with pharmaceutically acceptable, non-toxic carriers and/or auxiliary agents.The new composition is valuable in the human and veterinary practice for the treatment of patients suffering from infectious diseases.
    Type: Grant
    Filed: December 29, 1982
    Date of Patent: December 10, 1985
    Assignee: Leo Pharmaceutical Products Ltd.
    Inventor: Leif Tybring
  • Patent number: 4556669
    Abstract: Compounds of the formula ##STR1## wherein R is ##STR2## in which R.sub.1, R.sub.2 and R.sub.3 are the same or different and are selected from the group consisting of hydrogen, chlorine, bromine, lower alkyl, lower alkoxy and naphthyl, provided that when R.sub.1 is lower alkyl, R.sub.2 and R.sub.3 are hydrogen, chlorine, bromine or lower alkoxy, or a pharmaceutically acceptable salt thereof, have anti-carrageenin edema activity, and are useful as anti-inflammatory agents and immuno modulators. They are produced by reacting an amide of the formula ##STR3## wherein R has the same meanings hereinabove, with N,N'-ethylene thiourea.
    Type: Grant
    Filed: April 13, 1984
    Date of Patent: December 3, 1985
    Assignees: Kumiai Kagaku Kogyo Kabushiki Kaisha, Toyo Jozo Kabushiki Kaisha
    Inventors: Kazuo Nishio, Isao Chiyomaru, Katsuo Anma, Kazuko Yamamoto, Hiroshi Ohno, Noriyasu Takayanagi
  • Patent number: 4543358
    Abstract: This invention relates to aqueous gels, which remain gelatinous in a temperature range as low as -27.degree. C. containing dl- or 1-6-phenyl-2,3,5,6-tetrahydro(-)imidazo[2,1-b]thiazole, acylamino derivatives, thereof and pharmaceutically acceptable salts thereof, characterized by gelation and preparation at ambient temperatures (20.degree.-60.degree. C.), under vacuum, without additional heating or cooling in their preparation.
    Type: Grant
    Filed: August 26, 1983
    Date of Patent: September 24, 1985
    Assignee: American Cyanamid Company
    Inventor: James M. Quinlan
  • Patent number: 4536393
    Abstract: 6-alpha- and 6-beta-(Aminomethyl)penicillanic acid, 1,1-dioxide esters which are hydrolyzable under physiological conditions, particularly those wherein the ester radical is 1H-isobenzofuran-3-on-1-yl or (5-methyl-1,3-dioxol-2-on-4-yl)methyl, and an improved process and intermediates used in their synthesis.
    Type: Grant
    Filed: February 6, 1984
    Date of Patent: August 20, 1985
    Assignee: Pfizer Inc.
    Inventor: Wayne E. Barth
  • Patent number: 4525357
    Abstract: Novel derivatives of bicyclic 2-iminothiazolidine oximes and methods of preparing same. This invention is also directed to an insecticidal composition comprising an acceptable carrier and an insecticidally effective amount of a compound of this invention, as well as to a method of controlling insects which comprises subjecting the insects to an insecticidally effective amount of a compound of this invention.
    Type: Grant
    Filed: June 24, 1983
    Date of Patent: June 25, 1985
    Assignee: Union Carbide Corporation
    Inventors: Dean F. Bushey, Themistocles D. J. D'Silva
  • Patent number: 4512998
    Abstract: Compounds of the formula ##STR1## wherein R is alkyl having 1 to 4 carbon atoms, one of Y and Z is a heterocyclic moiety, and the other of Y and Z is hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms are useful as anthelmintics.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: April 23, 1985
    Assignee: Schering Corporation
    Inventor: M.Mehdi Nafissi-Varchei