Ring Nitrogen Is Shared By The Two Cyclos Patents (Class 548/154)
  • Patent number: 4376769
    Abstract: Disclosed herein are novel tetrahydro imidazo thiazoles, tetrahydro imidazo thiazines, hexahydro imidazo thiazepines and hexahydro imidazo thiazocines, intermediates for the preparation thereof, methods of using the compounds as anti-inflammatory agents and methods of using an intermediate thereof as anti-secretory agents to relieve the symptoms of gastric distress.
    Type: Grant
    Filed: June 19, 1981
    Date of Patent: March 15, 1983
    Assignee: Schering Corporation
    Inventor: Sherlock Margaret H.
  • Patent number: 4370482
    Abstract: A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives, and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of the anthelmintic levamisole, (-)-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazols, and its derivatives through conventional resolution procedures. The new process also permits the direct manufacture of optically active 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidone and their 3-acylated derivatives, optically active 1-(2-alkoxyethyl)-4-phenylimidazolidine-2-thiones, and levamisole, the levorotatory isomer of tetramisole, using catalytic amounts of a chiral reducing agent, with the elimination of conventional resolution procedures.
    Type: Grant
    Filed: October 28, 1981
    Date of Patent: January 25, 1983
    Assignee: American Cyanamid Co.
    Inventors: Sivaraman Raghu, Arthur K. Hoffmann, Balwant Singh
  • Patent number: 4353918
    Abstract: The invention relates to the dextrorotatory enantiomer of trans-5,6-di-p-methoxyphenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole and its pharmaceutically acceptable salts and to pharmaceutical preparations containing them.The new compounds have valuable pharmacological properties, especially anti-inflammatory and anti-rheumatic effects.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: October 12, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Richard Goschke, Pier G. Ferrini
  • Patent number: 4349683
    Abstract: Thiazolidine-2,4-dione derivatives, in the form of racemates or optically active isomers, corresponding to the formula (I) ##STR1## in which n=2 or 3, R.sub.1 =H, alkyl, benzoyl, acetyl or optionally substituted benzyl, R.sub.2 =H or alkyl, R.sub.3 =phenyl, which is optionally substituted by halogen, alkyl, alkoxy, NO.sub.2, CF.sub.3 or CF.sub.3 S, or naphthyl, and R.sub.4 =H, alkyl, phenyl, benzoyl or allyl, and acid addition salts thereof.These compounds are useful in therapy as anti-convulsants or anti-depressants.
    Type: Grant
    Filed: August 26, 1980
    Date of Patent: September 14, 1982
    Assignee: Synthelabo
    Inventor: Dennis C. Bigg
  • Patent number: 4349557
    Abstract: Thiazole derivatives of the general formula: ##STR1## wherein n represents 1 or 2 and each of X and Y independently of one another represents one or more substituents selected from hydrogen and halogen atoms, the trifluoromethyl radical and straight- or branched-chain alkyl and alkoxy radicals of 1 to 4 carbon atoms, are new therapeutically useful compounds, especially of interest in the treatment of depression.
    Type: Grant
    Filed: April 7, 1981
    Date of Patent: September 14, 1982
    Assignee: Synthelabo
    Inventor: Dennis Bigg
  • Patent number: 4340734
    Abstract: This disclosure describes certain novel 3-(.alpha.-substituted-benzyl)-2,3-dihydrothiazolo[3,2-a][1,3]diazacyclan- 3-ols which are useful as diuretic agents.
    Type: Grant
    Filed: November 14, 1980
    Date of Patent: July 20, 1982
    Assignee: American Cyanamid Company
    Inventors: Andrews S. Tomcufcik, William B. Wright, Jr., Joseph W. Marsico, Jr.
  • Patent number: 4327221
    Abstract: Novel 2-substituted-3-hydroxythiazolo[2,3-b]thiazolium salts, the mesoionic didehydro derivatives thereof and related compounds and their use as modulators of the immune response are disclosed.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: April 27, 1982
    Assignee: American Home Products Corporation
    Inventor: Peter H. L. Wei
  • Patent number: 4317832
    Abstract: Compounds corresponding to the formula ##STR1## are disclosed, wherein Alk represents a C.sub.2 -C.sub.5 -alkylene groups optionally substituted by a hydroxy group and Ar represent an optionally substituted phenyl, naphthyl, tetrahydronaphthyl, indanyl or indenyl radical or a monocyclic or condensed bicyclic or tricyclic heterocyclic radical which is optionally substituted, the heterocyclic radical consisting of individual rings having 5 or 6 members and optionally containing from 1 to 4 hetero atoms, and the acid addition salts thereof. A process for producing these compounds is also disclosed. These substituted aminoalkyl guanidines block the .beta.-receptors of the adrenergic nerve system, and also reduce blood pressure.
    Type: Grant
    Filed: September 5, 1979
    Date of Patent: March 2, 1982
    Inventors: Karl-Heinz Klingler, Axel Kleemann, Fritz Stroman, Klaus Thiemer
  • Patent number: 4315767
    Abstract: Triazolone herbicides of the formula: ##STR1## where V is hydrogen, fluorine, chlorine, bromine, methyl or OR where R is alkyl of 1-4 carbon atoms;X is hydrogen, fluorine, chlorine, bromine, cyano, methyl, methoxy, or nitro;Y is hydrogen, fluorine, chlorine, bromine, or methyl;n, m is 0, 1, 2, 3 or 4;Q is oxygen or sulfur;Z is oxygen, S(O).sub.p or NR';p is 0, 1 or 2 andR' is alkyl of 1-3 carbon atoms with the provisos that(1) n+m=2, 3, or 4; and(2) if n+m=2 or 4 then Y, X.noteq.Hand when Z is S(O)p, n is 1, 2, 3 or 4.
    Type: Grant
    Filed: December 14, 1979
    Date of Patent: February 16, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Anthony D. Wolf
  • Patent number: 4310672
    Abstract: A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of tetramisole, di-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives. The compound tetramisole is useful as an anthelmintic.
    Type: Grant
    Filed: March 17, 1980
    Date of Patent: January 12, 1982
    Assignee: American Cyanamid Co.
    Inventors: Sivaraman Raghu, Arthur K. Hoffmann, Balwant Singh
  • Patent number: 4282225
    Abstract: Thiazole derivatives of general formula (I) ##STR1## in which n is 1 or 2 and Ar represents a phenyl radical unsubstituted or substituted by one or more substituents selected from halogen atoms, the radical CF.sub.3, the phenyl radical straight or branched chain alkyl radicals having 1 to 4 carbon atoms, and cycloalkyl radicals having 3 to 6 carbon atoms, and their pharmaceutically acceptable acid addition salts are useful in therapy as anti-depressive agents. They are prepared by reacting the thiazole ##STR2## with a ketone X--CH.sub.2 --CO--CH.sub.2 O--Ar (III) (X is a leaving group, such as halogen).
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: August 4, 1981
    Assignee: Synthelabo
    Inventor: Dennis C. H. Bigg
  • Patent number: 4267339
    Abstract: There are disclosed certain novel imidazo(2,1-b)thiazoles, their physiologically acceptable acid addition--or quaternary ammonium salts and a process for their preparation. Said compounds show a good anti-diabetic activity.
    Type: Grant
    Filed: December 28, 1976
    Date of Patent: May 12, 1981
    Assignee: Plantex Ltd.
    Inventor: Enzo Tedeschi
  • Patent number: 4263311
    Abstract: The compounds are 5,6-phenyl-2,3-dihydroimidazo[2,1-b]thiazoles which have antiarthritic activity. A preferred compound is 5,6-bis(p-anisyl)-2,3-dihydroimidazo[2,1-b]thiazole.
    Type: Grant
    Filed: August 18, 1977
    Date of Patent: April 21, 1981
    Assignee: SmithKline Corporation
    Inventor: Paul E. Bender
  • Patent number: 4254259
    Abstract: By varying the acidity, solvent polarity, and temperature of the reaction of thiosemicarbazide with ethyl 4-chloroacetoacetate, ethyl 2-amino-6H-1,3,4-thiadiazine-5-acetate hydrochloride, ethyl 2-hydrazinothiazole-4-acetate, and ethyl 2-imino-3-aminothiazoline-4-acetate hydrochloride may be prepared selectively. Further derivatives may be prepared by benzoylation and nitrosation. These compounds have demonstrated utilities as herbicides.
    Type: Grant
    Filed: November 2, 1978
    Date of Patent: March 3, 1981
    Assignee: Indiana University Foundation
    Inventors: Ernest E. Campaigne, Thomas Selby
  • Patent number: 4242513
    Abstract: Chromogenic compounds of normally colorless form are disclosed having the following structural formula: ##STR1## wherein E represents a six-membered aromatic or heterocyclic ring which may have an aromatic condensed ring and both the E ring and the condensed ring may be substituted, A represents an optionally substituted aminophenyl, indolyl, benzoindolyl, julolidinyl or kairolyl radical or the radical represented by B, and B represents a family of heterocyclic radicals. The compounds of this invention are eligible for use in pressure-sensitive and heat sensitive record materials and manifold marking systems.
    Type: Grant
    Filed: March 5, 1979
    Date of Patent: December 30, 1980
    Assignee: Appleton Papers Inc.
    Inventors: Troy E. Hoover, Sheldon Farber, William J. Becker
  • Patent number: 4229461
    Abstract: This invention relates to fungicidal novel derivatives of 6-(3,5-dichlorophenyl)perhydroimidazo[5,1-b]thiazole derivative. These compounds may be used for controlling fungal infection, especially in agriculture.
    Type: Grant
    Filed: June 18, 1979
    Date of Patent: October 21, 1980
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Taichiro Shigematsu, Kenji Yoshida, Makoto Nakazawa, Hiroshi Kasugai, Masataka Tsuda
  • Patent number: 4204067
    Abstract: Compounds of the formula: ##STR1## and pharmaceutically acceptable acid addition salts thereof wherein R, R.sub.1, R.sub.2, R.sub.3, are selected from the group consisting of hydrogen, halogen and lower-alkyl of from one to four carbon atoms, inclusive; with the proviso that taken together they constitute the following substituents on the tetracydic ring, 10-halo, 8,10-dihalo, 8,9-di-lower-alkyl, and 7,9-dilower-alkyl; R', R'.sub.1, R'.sub.2, and R'.sub.3 are selected from the group consisting of hydrogen, halogen and lower alkyl of from one to four carbon atoms, inclusive, with the proviso that when taken together they constitute the following substituents, 1-halo, 2-halo, 3-halo, 4-halo, 1-lower-alkyl, 2-lower-alkyl, 3-lower-alkyl, 4-lower-alkyl, 1,3-dihalo, 2,3-dihalo, 2,4-dihalo, 3,4-dihalo, 1,3-di-lower-alkyl, 2,3-di-lower-alkyl, 1,4-di-lower-alkyl; R.sub.4, R.sub.5, R.sub.6, and R.sub.
    Type: Grant
    Filed: December 11, 1978
    Date of Patent: May 20, 1980
    Inventor: Parimal K. Adhikary
  • Patent number: 4168381
    Abstract: A method for the attainment of enhanced enantioselectivity in the reduction of 3-acyl derivatives of 1-(2-alkoxyethyl)-4-phenyl-imidazolin-2-ones to the optically active 3-acyl derivatives of 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones for use in the direct manufacture of levamisole, (-), 2, 3, 5, 6-tetrahydro-6-phenylimidazo-[2,1-b]-thiazole, useful as an anthelmintic has been discovered. The method involves the preferred use of iodide salts of Rh(I) complexes of optically active bis-tertiary phosphines to achieve maximum enantioselectivity. The methods for preparing the iodide salts are disclosed.
    Type: Grant
    Filed: April 14, 1978
    Date of Patent: September 18, 1979
    Assignee: American Cyanamid Company
    Inventors: Robert G. Fischer, Jr., Arnold Zweig, Sivaraman Raghu