Abstract: A novel crystalline monohydrate of 7-[D-.alpha.-amino-.alpha.-(p-hydroxyphenyl)acetamido]-3-methyl-3-cephem-4 -carboxylic acid is prepared and found to be a stable useful form of the cephalosporin antibiotic especially advantageous for pharmaceutical formulations.
Type:
Grant
Filed:
March 16, 1982
Date of Patent:
March 12, 1985
Assignee:
Bristol-Myers Company
Inventors:
Daniel Bouzard, Abraham Weber, Jacques Stemer
Abstract: Mitomycin A, mitomycin C, and porfiromycin react with amide acetals and other amide derivatives to produce amidine derivatives having antitumor activity against experimental animal tumors. The amidines derived from mitomycin C are useful intermediates in reactions with primary amines to produce both known and novel 7-amino-9a-methoxymitosanes having antitumor activity against experimental animal tumors.
Type:
Grant
Filed:
May 9, 1983
Date of Patent:
December 11, 1984
Assignee:
Bristol-Myers Company
Inventors:
Dolatrai M. Vyas, Takushi Kaneko, Terrence W. Doyle
Abstract: An antitumor antibacterial complex referred to as BBM-928 is described which is produced by microbiological fermentation under controlled conditions using a species of actinomycetes. The bioactive components of the complex have pronounced antitumor activity and are moderately to weakly active against gram-positive and acid fast bacteria but practically inactive against gram-negative bacteria and fungi. Based on median survival time, the component designated BBM-928A is substantially more active than mitomycin C by a factor of 10 to 300 fold against intraperitoneally implanted mouse tumors.
Abstract: Crude cephalosporin 7-[.alpha.-(2-aminomethylphenyl)acetamido]-3-[(1-carboxymethyltetrazol-5-y lthio)methyl]-3-cephem-4-carboxylic acid is purified by converting it to its salt with benzyldimethylamine, recovering said salt and from it regenerating said cephalosporin in purified form.
Abstract: 2.beta.-Chloromethyl-2.alpha.-methylpenam-3.alpha.-carboxylic acid sulfone and salts and esters thereof were synthesized and found to be potent inhibitors of .beta.-lactamases.
Abstract: The novel compound represented by the general formula (I) ##STR1## (wherein R represents a hydrogen atom, an alkanoyl group of 1 to 14 carbon atoms, or an arylcarbonyl group), and an acid addition salt thereof [on condition that when R is a hydrogen atom, the hydrochloride exhibits an optical rotation of [.alpha.].sub.D.sup.22 -1.degree. .+-.2.degree. (c, 2 water)] has antitumor activity in experimental animals.
Abstract: BBM-928A solutions suitable for parenteral use in animal experiments and having concentrations in the range of 1 mg/ml to 5 mg/ml are described.
Abstract: Bacteroides which are uniformly resistant to ceftazidime fail to grow when exposed to 2.beta.-chloromethyl-2.alpha.-methylpenam-3.alpha.-carboxylic acid (BL-P 2013), which itself is non-inhibitory, in combination with ceftazidime. Bacteroides infections are abated by treatment of the infected mammal with this combination of substances.
Abstract: Imidazopyrimidinones and other diazaheterocyclopyrimidinones having an additional fused imidazole or triazole ring have utility as bronchodilators, mediator release inhibitors, phosphodiesterase inhibitors, and peripheral vasodilators. They are orally active and useful in the prophylaxis and treatment of asthma. A preferred compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]-purin-9(4H)-one.
Abstract: N-Phenyl amidines which have diuretic, antithrombogenic, smooth muscle relaxant, anti-inflammatory and antiarrhythmic properties have been discovered. They are prepared by reacting a substituted aniline with a carboxamide selected from the group consisting of amides and lactams in the presence of phosphorus oxychloride. Typical examples of substituted N-phenyl amidines thus obtained are 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline, 2-(N-phenylbenzylamino)-1-pyrroline, 3-[(N-1-pyrrolin-1-yl-p-anisidino)methyl]indole and 4,5,6,7,8,9-hexahydro-2-(N-phenylphenethylamino)-3H-azonine. Indole substituted N-phenyl amidines can be rearranged to provide iminopyrrolinidinylindoles which are useful as diuretic, antithrombogenic and smooth muscle relaxant agents. In the case of 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole, the rearranged product is 3-[[2-p-methoxyphenylimino)-1-pyrrolidinyl]methyl]indole.
Abstract: Oral treatment with megestrol acetate improves survival rate and reduces the recurrence rate in the adjuvant therapy of breast cancer following mastectomy.
Type:
Grant
Filed:
September 1, 1976
Date of Patent:
January 25, 1983
Assignee:
Mead Johnson and Company
Inventors:
Martin O. Greaney, Merritt R. Callantine
Abstract: Piperazinyl derivatives containing a 3-alkylene-2,4-thiazolidinedione heterocyclic component with relatively selective psychotropic properties are disclosed. The compound 3-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,4-thiazolidinedione which has selective anxiolytic activity constitutes a typical embodiment of the invention.
Type:
Grant
Filed:
August 3, 1981
Date of Patent:
January 4, 1983
Assignee:
Mead Johnson & Company
Inventors:
Davis L. Temple, Jr., Richard E. Yeager
Abstract: Imidazopyrimidinones and other diazaheterocyclopyrimidinones having an additional fused imidazole or triazole ring have utility as bronchodilators, mediator release inhibitors, phosphodiesterase inhibitors, and peripheral vasodilators. They are orally active and useful in the prophylaxis and treatment of asthma. A preferred compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one.
Abstract: An antitumor antibacterial complex referred to as BBM-928 is described which is produced by microbiological fermentation under controlled conditions using a species of actinomycetes. The bioactive components of the complex have pronounced antitumor activity and are moderately to weakly active against gram-positive and acid fast bacteria but practically inactive against gram-negative bacteria and fungi. Based on median survival time, the component designated BBM-928A is substantially more active than mitomycin C by a factor of 10 to 300 fold against intraperitoneally implanted mouse tumors.
Abstract: New routes are provided for the synthesis of 3',4'-dideoxykanamycin B which is effective in inhibiting kanamycin-resistant organisms from kanamycin B through new intermediate, of which a fundamental process comprises a new reaction of a 3',4'-epoxy derivative of amino- and hydroxyl-protected kanamycin B with a xanthate to form a corresponding 3',4'-dideoxy-3'-eno derivative followed by removal of the amino- and hydroxyl-protecting groups thereof and by hydrogenation of the resulting 3',4'-dideoxy-3'-eno-kanamycin B. A 3',4'-episulfide derivative corresponding to the 3',4'-epoxy derivative which is formed as second product in the reaction of 3',4'-epoxy derivative with xanthate is also used as intermediate for the preparation of 3',4'-dideoxykanamycin B.
Type:
Grant
Filed:
September 15, 1980
Date of Patent:
November 2, 1982
Assignee:
Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
Abstract: Trimethylsilyl or another easily hydrolyzed ester of 6-trimethylsilyloxycarbonylaminopenicillanic acid was prepared by bubbling dry carbon dioxide into an anhydrous solution of the corresponding 6-trimethylsilylaminopenicillanate and found to be a useful intermediate in the production of penicillins, e.g., amoxicillin and ampicillin, by its acylation in anhydrous media with the appropriate acid chloride or acid chloride hydrochloride.
Type:
Grant
Filed:
August 13, 1981
Date of Patent:
September 28, 1982
Assignee:
Bristol-Myers Company
Inventors:
Derek Walker, Herbert H. Silvestri, Chester Sapino, David A. Johnson
Abstract: Novel spiro-quaternary ammonium halides are disclosed. The new compounds are particularly valuable as intermediates in preparation of N-(2-pyrimidinyl)piperazinylalkyl derivatives of azaspiroalkanediones such as the psychopharmacologic agent 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dio ne.
Type:
Grant
Filed:
October 16, 1980
Date of Patent:
September 28, 1982
Assignee:
Mead Johnson & Company
Inventors:
Jack C. Simms, deceased, Old National Bank in Evansville, administrator
Abstract: 4-Ethyl-6-methoxy-7-(oxiranylmethoxy)quinazoline and its isomer 4-ethyl-7-methoxy-6-(oxiranylmethoxy)quinazoline have potent anti-tumor activity in animals.
Type:
Grant
Filed:
March 6, 1981
Date of Patent:
August 10, 1982
Assignee:
Mead Johnson & Company
Inventors:
William E. Kreighbaum, William T. Comer
Abstract: A novel crystalline monohydrate of 7-[D-.alpha.-amino-.alpha.-(p-hydroxyphenyl)acetamido]-3-methyl-3-caphem-4 -carboxylic acid is prepared and found to be astable useful form of the cephalosporin antibiotic especially advantageous for pharmaceutical formulations.
Type:
Grant
Filed:
November 30, 1982
Date of Patent:
November 13, 1984
Assignee:
Bristol-Myers Company
Inventors:
Daniel Bouzard, Abraham Weber, Jacques Stemer