Abstract: Compounds of the formula ##STR1## or pharmaceutically acceptable acid-addition or quaternart ammonium salts thereofwhereinR is hydroxy, carboxy, lower alkoxycarbonyl, benzyloxycarbonyl, phenoxycarbonyl, carbamoyl, N-loweralkyl-carbamoyl, N,N-dilower-alkyl-carbamoyl, carboazido, carbohydrazido or cyano;R.sup.2 is C.sub.1 to C.sub.6 alkyl;R.sup.3 is C.sub.1 to C.sub.6 alkyl or benzyl; andR.sup.4 is a single electron pair, hydrogen or lower alkyl; and the dotted lines represent saturated or unsaturated bonds, are disclosed with analgesic properties.
Type:
Grant
Filed:
March 14, 1980
Date of Patent:
September 22, 1981
Assignee:
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
Inventors:
Jozsef Knoll, Zoltan Meszaros, Istvan Hermecz, Ferenc Fulop, Gabor Bernath, Sandor Virag, Gabor Nagy, Peter Szentmiklosi
Abstract: Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein one of R.sub.1 and R.sub.2 represents a lower alkyl group, a phenyl group, a halophenyl group, or a lower alkoxyphenyl group and the other of them represents a hydrogen atom, a lower alkyl group, or a phenyl lower alkyl group; said R.sub.1 and R.sub.2 may combine with each other to form a trimethylene group or a tetramethylene group; R.sub.3 represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl lower alkyl group; X represents an oxygen atom, a sulfur atom, an imino group, or a group shown by ##STR2## (wherein m represents 1 or 2 and R.sub.4 represents a lower alkyl group, a hydroxy lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group); and Y represents an ethylene group which may be substituted by lower alkyl group, a trimethylene group, a tetramethylene group, a vinylene group which may be substituted by a lower alkyl group, or ##STR3## (wherein R.sub.
Abstract: Novel substituted 2,3-alkylene bis (oxy) benzamides and derivatives thereof are disclosed. Also disclosed is a method for producing said compounds. The compounds have anxiolytic, psychostimulant, disinhibiting and thymoanaleptic properties useful therapeutically in the psychofunctional field, particularly in gastro-enterology, cardiology, urology, rheumatology and gynaecology.
Type:
Grant
Filed:
February 23, 1979
Date of Patent:
May 19, 1981
Assignee:
Societe d'Etudes Scientifiques et Industrielles de l'Ile-de-France
Inventors:
Michel Thominet, Gerard Bulteau, Jacques Acher, Claude Collignon
Abstract: Antiallergic and antiasthmatic compounds of the formula ##STR1## of which 9-phenylamino-6-methyl-4-oxo-6,7-dihydro-4H-pyrido(1,2-a)pyrimidine-3-carb oxylic acid and optically active antipodes and salts thereof are examples.
Type:
Grant
Filed:
December 11, 1978
Date of Patent:
April 7, 1981
Assignee:
Chinoin Gyogyszer es Vecyeszeti Termekek Gyara Rt.
Inventors:
Istvan Hermecz, Zoltan Meszaros, Tibor Breining, Sandor Virag, Lelle Vasvari nee Debreczi, Agnes Horvath, Gabor Nagy, Attila Mandi, Tamas Szuts, Istvan Bitteer, Gyula Sebestyen
Abstract: An optically active or racemic fused pyrimidine derivative of the formula I ##STR1## has pharmaceutical activity in decreasing serum lipids, cholesterol deposits and, in general, against atherosclerosis.
Type:
Grant
Filed:
August 8, 1978
Date of Patent:
February 24, 1981
Assignee:
Chincin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
Inventors:
Istvan Hermecz, Zoltan Meszaros, Sandor Virag, Lelle Vasvari, Agnes Horvath, Jozsef Knoll, Gyula Sebestyen, Agoston David
Abstract: Antiallergic and particularly antiasthmatic compounds of the formula: ##STR1## of which 9-phenylhydrazono-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimi dine-3-carboxylic acid is an especially significant example.
Type:
Grant
Filed:
December 11, 1978
Date of Patent:
November 18, 1980
Assignee:
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
Inventors:
Istvan Hermecz, Zoltan Meszaros, Tibor Breining, Sandor Virag, Lelle V. Vasvari nee Debreczy, Agnes Horvath, Gabor Nagy, Attila Mandi, Tamas Szucs, Istvan Bitter, Gyula Sebestyen
Abstract: Compounds of the formula: ##STR1## or pharmaceutically acceptable acid addition or quaternary ammonium salts thereofwhereinR.sup.2 is C.sub.1 to C.sub.6 alkyl:R.sup.3 is C.sub.1 to C.sub.6 alkyl;R.sup.4 is a single electron pair, hydrogen or lower alkyl; and the dotted lines indicate saturated or unsaturated bonds, are disclosed with analgesic properties.
Type:
Grant
Filed:
August 17, 1978
Date of Patent:
August 26, 1980
Assignee:
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara RT
Inventors:
Josef Knoll, Zoltan Meszaros, Istvan Hermecz, Ferenc Fulop, Gabor Bernath, Sandor Virag, Gabor Nagy, Peter Szentmiklosi
Abstract: The use of 3-aryl-thiazolo[3,2-a]benzimidazoles, 3-aryl-imidazo[2,1-b]thiazoles, and related compounds as antineoplastic agents, and/or as enhancers of the immune response is disclosed.
Type:
Grant
Filed:
July 18, 1978
Date of Patent:
July 22, 1980
Assignee:
American Home Products Corporation
Inventors:
Richard L. Fenichel, Peter H. L. Wei, Francis J. Gregory, Harvey E. Alburn
Abstract: Pyrida-(1,2A)-pyrimidine-derivatives and a process for preparing these compounds are disclosed. These compounds possess analgesic, anti-inflammatory, and anti-pyretic properties as well as the ability to depress the central nervous system.
Type:
Grant
Filed:
March 19, 1975
Date of Patent:
June 24, 1980
Assignee:
Chinoin Gygyszer es Vegyeszeti Termekek Gyara Rt.
Abstract: Disclosed are O- derivatives (esters and ethers of the secondary alcohol group) of the antibiotic thienamycin which has the following structure: ##STR1## Such derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such derivatives, pharmaceutical compositions comprising such derivatives, and methods of treatment comprising administering such derivatives and compositions when an antibiotic effect is indicated.
Type:
Grant
Filed:
December 16, 1977
Date of Patent:
June 17, 1980
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, William J. Leanza
Abstract: Disclosed are substituted N-methylene derivatives of thienamycin which may be represented by the following structural formula: ##STR1## wherein X and Y are selected from the group consisting of hydrogen, R, OR, SR, and NR.sup.1 R.sup.2 wherein, inter alia, R is substituted or unsubstituted: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl, and heterocyclylalkyl; R.sup.1 and R.sup.2 are hydrogen or R. Such compounds and their pharmaceutically acceptable salt, ether, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
Type:
Grant
Filed:
November 17, 1977
Date of Patent:
March 18, 1980
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, William J. Leanza, Kenneth J. Wildonger
Abstract: A novel series of optionally substituted 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-N-(1H-tetrazol-5-yl)carboxamides is provided for use as inhibitors of allergic reactions. The compounds exhibit antiallergy activity by both oral and parenteral routes of administration.
Abstract: Aromatic urethanes are produced by interacting an aromatic nitro compound, an organic compound containing hydroxyl groups and carbon monoxide in the presence of a catalyst composed of elemental selenium or a selenium compound and of a promoter composed of a bicyclic amidine together with a phenolic compound or a carboxylic acid. The interaction proceeds smoothly with the aid of a small amount of the promoter, attended with secondary production of amino compounds only in small amounts. For instance, 2,4-diethyldicarbamatetoluene is obtained at a yield of 87% by interacting 2,4-dinitrotoluene, ethanol and carbon monoxide in the presence of a catalytic system composed of metallic selenium, 1,8-diazabicyclo(5,4,0)-undecene-7 and acetic acid.
Abstract: Through total synthesis methods developed in the assignee's laboratories, new as well as old penicillin and cephalosporin compounds (all containing the beta-lactam functional group) have been prepared. One of the key intermediates prepared by total synthesis has the 7-amino (6-amino in the case of a penicillin derivative) group in the alpha configuration. The instant invention provides a general route for preparing the 7.beta.-amino (or 6.beta.-amino) compound, through the formation of an imino-containing intermediate, followed by hydrolysis to the desired epimer. Novel intermediate products are provided. The compounds having the desired beta epimer can be converted to acylaminoantibiotics.
Abstract: Disclosed are N-alkylated derivatives of thienamycin sulfoxide (I, n=1) and sulfone (I, n=2): ##STR1## wherein n=1 or 2; and R.sup.5, R.sup.6, and R.sup.7 are, inter alia, hydrogen or alkyl. Such compounds the their pharmaceutically acceptable O- and carboxyl- derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such derivatives, pharmaceutical compositions comprising such derivatives and methods of treatment comprising administering such derivatives and compositions when an antibiotic effect is indicated.
Type:
Grant
Filed:
September 15, 1977
Date of Patent:
April 17, 1979
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, Raymond A. Firestone, William J. Leanza
Abstract: Disclosed are antibiotic 3-(substituted thio)-7-(substituted methyl) cephalosporins, derivatives and analogues thereof; wherein the methyl substituent is, inter alia, hydroxyl, ketonic oxygen, imino nitrogen, amino or mercapto. Also disclosed are processes for the preparation of such compounds and their pharmaceutically acceptable salt, ester and amide derivatives; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
Type:
Grant
Filed:
May 8, 1978
Date of Patent:
April 17, 1979
Assignee:
Merck & Co., Inc.
Inventors:
Thomas R. Beattie, Lovji D. Cama, Burton G. Christensen, Frank P. Dininno
Abstract: Compounds of the formula: ##STR1## or pharmaceutically acceptable salts thereof are disclosed wherein R is hydrogen or C.sub.1 to C.sub.6 alkyl;R.sup.2 and R.sup.3 are each hydrogen or together form a valency bond;R.sup.6 is carboxy or C.sub.1 to C.sub.6 alkoxycarbonyl;R.sup.7 and R.sup.8 are each hydrogen or together form a valency bond;R.sup.10 is carboxy or C.sub.1 to C.sub.6 alkoxycarbonyl and the dotted line represents two hydrogen atoms or a valency bond. The compounds are useful in the treatment of atherosclerosis.
Type:
Grant
Filed:
February 4, 1977
Date of Patent:
October 31, 1978
Assignee:
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.
Inventors:
Istvan Hermecz, Zoltan Meszaros, Sandor Virag, Lelle Vasvari nee Debreczy, Agnes Horvath, Jozsef Knoll, Gyula Sebestyen, Agoston David
Abstract: A novel series of optionally substituted 3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-ones is provided for use as inhibitors of allergic reactions. The compounds exhibit antiallergy activity by both oral and parenteral routes of administration.
Abstract: Compounds of the formula ##STR1## where A is a heterocyclic group containing a pyridone moiety and R to R.sup.5 are each hydrogen or substituents conventionally encountered in dyes. The compounds are eminently suitable for coloring resins and for dyeing textile materials, particularly polyester textile materials.