Benzothiazines (including Hydrogenated) Patents (Class 544/49)
  • Patent number: 4294961
    Abstract: Certain benzothiazine compounds, metal complexes thereof and solutions of said compounds in essentially water-immiscible, liquid hydrocarbon solvents are disclosed. These compounds have in their 4-keto form, the structure: ##STR1## the corresponding enol of which has the structure: ##STR2## wherein x, n, R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification and claims hereof. Particular metal values are recovered from their aqueous solutions by using the benzothiazine compounds dissolved in essentially water-immiscible, liquid hydrocarbon solvents. The extraction process involves contacting the metal value containing aqueous solution with the solution of the benzothiazine in essentially water-immiscible, liquid hydrocarbon solvent and stripping the metal from the loaded organic phase.
    Type: Grant
    Filed: April 7, 1980
    Date of Patent: October 13, 1981
    Assignee: Henkel Corporation
    Inventor: Ernest Spitzner
  • Patent number: 4289879
    Abstract: 2-Methoxyethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide is an advantageous ester precursor for piroxicam (4-hydroxy-2-methyl-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide), an antiinflammatory agent established in medical practice.
    Type: Grant
    Filed: September 29, 1980
    Date of Patent: September 15, 1981
    Assignee: Pfizer Inc.
    Inventor: Joseph G. Lombardino
  • Patent number: 4233299
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, methyl or ethyl;R.sub.2 is methyl, ethyl or n-propyl; andY is hydrogen, methyl, methoxy, fluorine or chlorine;and non-toxic, pharmacologically acceptable salts thereof formed with an inorganic or organic base. The compounds as well as their salts are useful as antiphlogistics.
    Type: Grant
    Filed: December 6, 1978
    Date of Patent: November 11, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Gunter Trummlitz, Wolfhard Engel, Ernst Seeger, Gunther Engelhardt
  • Patent number: 4213980
    Abstract: 3,4-Dihydro-2H-1,2-benzothiazine 1,1-dioxides of the formula ##STR1## wherein Ph represents a substituted or unsubstituted 1,2-phenylene radical, R represents a substituted or unsubstituted benzopyrone radical, and R.sub.1 represents hydrogen or a substituted or unsubstituted hydrocarbon radical of aliphatic character, and their salts, possess antiinflammatory properties and are useful as medicaments.
    Type: Grant
    Filed: January 17, 1979
    Date of Patent: July 22, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Alex Sele, Pier G. Ferrini, Georges Haas, Knut A. Jaeggi, Alberto Rossi
  • Patent number: 4116964
    Abstract: A novel process for preparing 4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides is disclosed. The process involves the base catalyzed rearrangement of a saccharinacetamide of structure I to give II, ##STR1## wherein R.sup.1 is hydrogen or lower alkyl and R.sup.2 is lower alkyl, aryl or a heterocyclic ring selected from the group consisting of pyridyl, substituted-pyridyl, and thiazolyl. Compounds of the formula II have useful anti-inflammatory properties. In addition, they can be used as intermediates in the preparation of known anti-inflammatory agents.
    Type: Grant
    Filed: August 16, 1977
    Date of Patent: September 26, 1978
    Assignee: Warner-Lambert Company
    Inventors: Harold Zinnes, Neil A. Lindo, John Shavel, Jr.
  • Patent number: 4100347
    Abstract: Process for production of 3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxylic acid-1,1-dioxide by hydrolysis, in the presence of hydroxide ions, of an alkyl or aralkyl ester thereof followed by precipitation of the acid at pH below 6.0 and its use as an intermediate for the production of N-(2-pyridyl)-3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxamid e-1,1-dioxide and the analogous N-(2-thiazolyl)-compound, effective antiinflammatory agents.
    Type: Grant
    Filed: June 10, 1976
    Date of Patent: July 11, 1978
    Assignee: Pfizer Inc.
    Inventor: Philip D. Hammen
  • Patent number: 4074048
    Abstract: A novel process for preparing 4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides is disclosed. The process involves the base catalyzed rearrangement of a saccharinacetamide of structure I to give II, ##STR1## wherein R.sup.1 is hydrogen or lower alkyl and R.sup.2 is lower alkyl, aryl or a heterocyclic ring selected from the group consisting of pyridyl, substituted-pyridyl, and thiazolyl. Compounds of the formula II have useful anti-inflammatory properties. In addition, they can be used as intermediate in the preparation of known anti-inflammatory agents.
    Type: Grant
    Filed: May 10, 1976
    Date of Patent: February 14, 1978
    Assignee: Warner-Lambert Company
    Inventors: Harold Zinnes, Neil A. Lindo, John Shavel, Jr.
  • Patent number: RE29669
    Abstract: A process for the synthesis of N-aryl-3,4-dihydro-2-alkyl-4-oxo-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides by treatment of N-aryl-N'-alkyl-N'-(2'-alkoxycarbonylbenzenesulfonyl)glycineamides, useful intermediates for said process, with an alkali or alkaline earth metal hydride in a reaction-inert solvent at 50.degree.-150.degree. C., said products being antiinflammatory agents.
    Type: Grant
    Filed: November 30, 1976
    Date of Patent: June 13, 1978
    Assignee: Pfizer, Inc.
    Inventor: Joseph G. Lombardino
  • Patent number: RE29836
    Abstract: Compounds having the following structural formula are disclosed: ##STR1## wherein R.sub.1 is hydrogen or methyl and R.sub.2, and R.sub.3 are hydrogen or alkyl. These compounds are useful as anti-inflammatory agents, antipyretics, analgesics.
    Type: Grant
    Filed: October 11, 1977
    Date of Patent: November 14, 1978
    Assignee: Warner-Lambert Company
    Inventors: Harold Zinnes, Martin L. Schwartz, John Shavel, Jr.