Abstract: The present invention relates to novel thiazolidinone acetic acid derivatives and their preparation. These derivatives show diuretic properties when used as pharmaceuticals.
Type:
Grant
Filed:
March 18, 1976
Date of Patent:
August 9, 1977
Assignee:
Warner-Lambert Company
Inventors:
Gerhard Satzinger, Manfred Herrmann, Karl-Otto Vollmer
Abstract: A novel process for preparing 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide (I), starting with 3-amino-5-methylisoxazole (II) is disclosed. Compound I exhibits anti-inflammatory properties and is useful for treating inflammation. In the process of the invention an intermediate obtained, 2,3-dihydro-N-(5-methyl-3-isoxazolyl)-3-oxo-1,2-benzisothiazole-2-acetamid e 1,1-dioxide (IV) undergoes rearrangement to provide 1-{[5-(4-hydroxy-2H-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]methyl}eth anone S,S-dioxide (V), which is methylated, according to conventional procedures. The methylated intermediate VI, upon further treatment, undergoes a second rearrangement to obtain the desired anti-inflammatory compound I.
Type:
Grant
Filed:
December 29, 1975
Date of Patent:
August 9, 1977
Assignee:
Warner-Lambert Company
Inventors:
Arthur C. Fabian, Jerome D. Genzer, Charles Francis Kasulanis, John Shavel, Jr., Harold Zinnes
Abstract: The present invention relates to 2-[1-imino-2-(methylsulfinyl)ethyl]phenols and 3-[1-imino-2-(methylsulfinyl)ethyl]-2-naphthalenols having the following structural formulas: ##STR1## wherein X is hydrogen, lower alkyl, halogen, lower alkoxy or hydroxy; Y is hydrogen, lower alkyl or cycloalkyl.These compounds exhibit antibacterial activity, particularly against gram-positive bacteria, and are useful in the treatment of bacterial infections caused by these organisms.
Type:
Grant
Filed:
December 8, 1976
Date of Patent:
August 2, 1977
Assignee:
Warner-Lambert Company
Inventors:
David T. Connor, Patricia A. Young, Max VON Strandtmann
Abstract: The present invention relates to novel thiazolidinone acetic acid derivatives and their preparation. These derivatives show diuretic properties when used as pharmaceuticals.
Type:
Grant
Filed:
March 18, 1976
Date of Patent:
August 2, 1977
Assignee:
Warner-Lambert Company
Inventors:
Gerhard Satzinger, Manfred Herrmann, Karl-Otto Vollmer
Abstract: A portable medical data strip chart recorder in which a drive roller for drawing the strip across a platen includes integral motive means for rotating the roller at a selected angular velocity. A D.C. motor is mounted internally and concentrically with the roller shaft which upon energization drives the roller and hence the strip paper at a desired linear velocity. The incorporation of a D.C. motor internally of the drive shaft permits reduction in size and weight of the recorder as well as achieving a more efficient drive power transmission.
Abstract: The present invention is concerned with novel tricyclic sulphoximides and with the preparation thereof. This family of compounds has been found to possess antihistominic, antitussive, antiinflammatory, sedative, and diuretic properties.
Abstract: This invention relates to novel compounds of the pyrido-[2,1-b]-quinazolin-one series and their methods of preparation. These compounds have utility as antiallergy agents.
Abstract: 15-Cycloalkyl-prostaglandins of the formula:- ##STR1## wherein A represents a grouping of the formula:- ##STR2## X represents ethylene of cis-vinylene, Y represents ethylene or trans-vinylene, B represents ethylene or trans-vinylene, R represents hydrogen or alkyl of 1 through 4 carbon atoms, R.sup.1 represents cycloalkyl of 4 through 7 carbon atoms, and R.sup.2 represents hydrogen or alkyl of 1 through 12 carbon atoms, are new compounds possessing the useful pharmacological properties typical of prostaglandins; they are of especial interest in the inhibition of blood platelet aggregation.
Abstract: The present invention relates to [2-(4-oxo-4H-1-benzopyran-2-yl)ethenyl]benzonitrile and benzoic acids having the following structural formula: ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are hydrogen, lower alkyl, halogen or lower alkoxy, and A is COOH or CN. The compounds of this invention exhibit anti-allergy properties and are indicated in the management of allergic manifestations such as bronchial asthma.
Type:
Grant
Filed:
November 20, 1975
Date of Patent:
July 5, 1977
Assignee:
Warner-Lambert Company
Inventors:
Marvin P. Cohen, John Shavel, Jr., Max VON Strandtmann
Abstract: This invention relates to novel indolothiopyrones having the formula: ##STR1## wherein R.sub.1 is hydrogen, lower alkyl or aryl; R.sub.2 is hydrogen or halogen; and R.sub.7 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, nitro-substituted-aryl, or .omega.-substituted lower alkyl wherein the substituent is: ##STR2## wherein R.sub.4 and R.sub.5 each represent hydrogen, lower alkyl, or together with the nitrogen atom, form a heterocyclic ring; and R.sub.6 is lower alkoxy or amino, and novel intermediates used in their preparation. The indolothiopyrones are prepared by reacting a 3-mercaptoindole with sodium propiolate or a substituted sodium propiolate followed by acidification to obtain an intermediate acid; the intermediate acid cyclizes in the presence of an acid catalyst to obtain the indolothiopyrone structure which may be additionally subjected to halogenation, alkylation or hydrolysis to obtain derivatives having the various substituent groups disclosed.
Abstract: The present invention relates to a process for 3r-N-Monomethylamino-4 cis-phenyl-4 trans-ethoxycarbonyl-cyclohexene and its N-substitution products which are generally useful as analgesics.
Abstract: An improved process for the preparation of 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide (I), a known anti-inflammatory agent, is described. The process involves the reaction of a solution of alkyl 2,3-dihydro-3-oxo-1,2-benzisothiazole-2-acetate 1,1-dioxide (II) in dimethylformamide, with an alkali metal alkoxide using the specific portions of reactants and carefully controlled reaction conditions. Acidification of the reaction mixture precipitates out alkyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (III) in substantially pure form in high yields, without recrystallization. Product III is methylated on the sulfonamide nitrogen and reacted with 3-amino-5-methylisoxazole to obtain crude I. A further improvement in the process of the invention involves a more efficient method for purifying crude product I by solubilizing in dimethylformamide with heating to 125.degree. C. to 148.degree. C.
Type:
Grant
Filed:
March 10, 1976
Date of Patent:
May 17, 1977
Assignee:
Warner-Lambert Company
Inventors:
Jerome Daniel Genzer, Francisco Carrio Fontsere
Abstract: This invention relates to substituted 2-amino chromones of the general structure I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 may be hydrogen, hydroxy, lower alkyl or lower alkoxy of 1-6 carbon atoms, halogen such as chloro or bromo, or aryl such as phenyl, and X may be cyano or carboxamido. Two novel procedures for preparing substituted 2-amino chromones having the Formula I, starting with salicylic acid or substituted salicylic acid, are described. The compounds of this invention are active in the prevention of allergic and asthmatic reactions in mammals.
Abstract: Trans-.DELTA..sup.2 -prostaglandin compounds are disclosed of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## R.sup.1 represents an alkyl group containing from 1 to 10 carbon atoms, or an alkyl group containing from 1 to 6 carbon atoms carrying a phenyl substituent or a cycloalkyl substituent of 5 to 7 carbon atoms, R.sup.2 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, and R.sup.3.sup.' represents a hydrogen atom or an alkyl group containing from 1 to 12 carbon atoms, the double bonds in the 2- and 5-positions being in the trans- and cis-configurations respectively. These compounds are indicated in the management of conditions such as autoimmune conditions, e.g. rheumatoid arthritis.
Abstract: A novel process for preparing 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide (I), starting with 3-amino-5-methylisoxazole (II) is disclosed. Compound I exhibits anti-inflammatory properties and is useful for treating inflammation. In the process of the invention an intermediate obtained, 2,3-dihydro-N-(5-methyl-3-isoxazolyl)-3-oxo-1,2-benzisothiazole-2-actamide 1,1-dioxide (IV) undergoes rearrangement to provide 1-{[5-(4-hydroxy-2H-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]methyl}eth anone, S,S-dioxide (V), which is methylated, according to conventional procedures. The methylated intermediate VI, upon further treatment, undergoes a second rearrangement to obtain the desired anti-inflammatory compound I.
Type:
Grant
Filed:
December 29, 1975
Date of Patent:
May 10, 1977
Assignee:
Warner-Lambert Company
Inventors:
Arthur C. Fabian, Jerome D. Genzer, Charles Francis Kasulanis, John Shavel, Jr., Harold Zinnes
Abstract: A dimensionally stable, shaped eye bandage for medicament delivery comprises polymerized random graft copolymers containing (in the dry state) from 67.2% to 79.3% HEMA; from 14.25% to 35% PVP; from 0.1% to 4.04% EDMA; from 0.1% to 2.5% MA; from 0.1% to 5.0% water; from 0 to 4 ppm HQ inhibitor; and from 50 to 250 ppm MEHQ inhibitor. The eye bandage composition contains from 45% to 65% water after hydration. An improved method for shaping, polymerizing, and cutting and hydrating the eye bandage composition is provided. The polymerization is conducted using only a low temperature initiator, by de-gassing prior to polymerization to remove substantially all oxygen, and by conducting the initial polymerization reaction at from 23.degree. C to 30.degree. C for 16 to 30 hours, during which the heat of the reaction is continuously absorbed to control the reaction exotherm.
Type:
Grant
Filed:
March 1, 1976
Date of Patent:
May 10, 1977
Assignee:
Warner-Lambert Company
Inventors:
Albert R. LeBoeuf, William R. Grovesteen
Abstract: This invention relates to 4r-amino-1t-phenyl-1c-ethoxycarbonyl-cyclohexenes-(2) of formula I: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and are hydrogen or alkyl having 1 to 4 carbon atoms, or one of the two groups is allyl, phenalkyl having 7 to 9 carbon atoms or .alpha.-methyl-.beta.-hydroxyethyl; or R.sub.1 and R.sub.2 together form a morpholino group, piperazino group substituted at the 4- position by methyl, benzyl, phenyl, 3-chlorophenyl, 4-chlorophenyl, 2-phenethyl or benzoyl, or a piperidino group substituted at the 4- position by hydroxyl, phenyl, 2-methoxyphenyl, 4-methoxyphenyl, methyl or benzyl and medically acceptable addition compounds derived from inorganic and organic acids or lower alkyl halides. The compounds of the present invention are prepared by separation of 4-amino-1-phenyl-1-ethoxycarbonyl-cyclohexenes-(2), described in U.S. Pat. application Ser. No. 226,509, filed Feb. 15, 1972, now U.S. Pat. No. 3,957,851 into the two possible geometrical isomers.
Abstract: A novel process for preparing 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide (I), starting with 3-amino-5-methylisoxazole (II) is disclosed. Compound I exhibits anti-inflammatory properties and is useful for treating inflammation. In the process of the invention an intermediate obtained, 2,3-dihydro-N-(5-methyl-3-isoxazolyl)-3-oxo-1,2-benzisothiazole-2-acetamid e 1,1-dioxide (IV) undergoes rearrangement to provide 1-{[5-(4-hydroxy-2H-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]methyl}eth anone S,S-dioxide (V), which is methylated, according to conventional procedures. The methylated intermediate VI, upon further treatment, undergoes a second rearrangement to obtain the desired anti-inflammatory compound I.
Type:
Grant
Filed:
June 18, 1976
Date of Patent:
April 19, 1977
Assignee:
Warner-Lambert Company
Inventors:
Arthur C. Fabian, Jerome D. Genzer, Charles Francis Kasulanis, John Shavel, Jr., Harold Zinnes