Patents Represented by Attorney Frank P. Hoffman
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Patent number: 4520195Abstract: There is presented compounds of the formula ##STR1## wherein X represents the 1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-as-triazin-3-yl group or its corresponding tautomeric form, the 2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl group,and the readily hydrolyzable esters, readily hydrolyzable ethers and salts of the compounds and hydrates of the compounds of formula I or of their esters, ethers and salts. Also provided is a method of their manufacture and intermediates therefor as well as corresponding pharmaceutical preparations.Type: GrantFiled: August 1, 1983Date of Patent: May 28, 1985Assignee: Hoffmann-La Roche Inc.Inventor: Roland Reiner
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Patent number: 4518784Abstract: There is presented a process for the manufacture of hexahydronaphthacene derivatives of the general formula ##STR1## wherein one of R.sup.1 and R.sup.2 represents a hydrogen atom and the other represents a hydrogen atom or a hydroxy group of R.sup.1 and R.sup.2 together represent a protected oxo group, R.sup.3 represents a hydrogen atom or a hydroxy or acyloxy group and R.sup.4 represents a lower alkyl or esterified carboxy group or a group of the formula ##STR2## wherein R.sup.5 and R.sup.6 together form an oxo group or a protected oxo group and X represents a hydrogen atom or a hydroxy or acyloxy group or ##STR3## in which n stands for 1 or 2 and Y represents a hydrogen atom or an alkyl or acyl group.Also presented are certain of the novel derivatives per se and various novel intermediates in the process.Type: GrantFiled: February 23, 1984Date of Patent: May 21, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Michael J. Broadhurst, Cedric H. Hassall, Gareth J. Thomas
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Patent number: 4515969Abstract: There is presented a process for the manufacture of hexahydronaphthacene derivatives of the general formula ##STR1## wherein one of R.sup.1 and R.sup.2 represents a hydrogen atom and the other represents a hydrogen atom or a hydroxy group or R.sup.1 and R.sup.2 together represent a protected oxo group, R.sup.3 represents a hydrogen atom or a hydroxy or acyloxy group and R.sup.4 represents a lower alkyl or esterified carboxy group or a group of the formula ##STR2## wherein R.sup.5 and R.sup.6 together form an oxo group or a protected oxo group and X represents a hydrogen atom or a hydroxy or acyloxy group or ##STR3## in which n stands for 1 or 2 and Y represents a hydrogen atom or an alkyl or acyl group.Also presented are certain of the novel derivatives per se and various novel intermediates in the process.Type: GrantFiled: January 23, 1984Date of Patent: May 7, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Michael J. Broadhurst, Cedric H. Hassall, Gareth J. Thomas
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Patent number: 4512999Abstract: There are presented .beta.-lactams of the formula ##STR1## wherein R.sup.1 is cyano or a group of the formula R.sup.4 --CO-- or R.sup.5 --A--CO--, R.sup.2 is hydrogen, lower alkyl or halogen, R.sup.3 is hydrogen or a group readily cleavable by hydrolysis, n is the number 0, 1 or 2, R.sup.4 is hydrogen, hydroxy, lower alkoxy, lower alkyl, aryl or a group of the formula ##STR2## R.sup.5 is halogen, lower alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl or di-(loweralkoxy)phoshinyl, R.sup.6 and R.sup.7 are lower alkyl and A is lower alkylene,and pharmaceutically acceptable salts of carboxylic acids of formula I with bases.The compounds exhibit pronounced .beta.-lactamase-inhibiting properties.Type: GrantFiled: October 20, 1981Date of Patent: April 23, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Solange Adam-Molina, Werner Hofheinz
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Patent number: 4489003Abstract: There are described novel pharmaceutically active substances which have a pronounced affinity to the central benzodiazepine receptors and which have only a low toxicity.These active substances, namely imidazobenzodiazepines of the formula ##STR1## wherein A is lower alkylene, n is zero or 1, R.sup.1 is lower alkynyl, lower alkenyl, aryl, (C.sub.3-8)-cycloalkyl optionally substituted by lower alkyl or (C.sub.5-8)-cycloalkenyl optionally substituted by lower alkyl, or a 5- or 6-membered saturated or unsaturated heterocycle which contains an oxygen or sulphur atom as a ring member and which is optionally substituted by lower alkyl, R.sup.4 and R.sup.5 each are hydrogen, halogen, trifluoromethyl, cyano, nitro, amino or lower alkyl and either R.sup.2 is hydrogen and R.sup.3 is lower alkyl or R.sup.2 and R.sup.3 together are dimethylene, trimethylene or propenylene, the compounds of formula I in which R.sup.2 and R.sup.Type: GrantFiled: July 14, 1983Date of Patent: December 18, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Walter Hunkeler, Emilio Kyburz
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Patent number: 4482551Abstract: There is presented compounds of the formula ##STR1## in which R.sup.1 represents hydrogen or methyl, as well as readily hydrolyzable esters and salts of these compounds and the hydrates thereof.Also presented are various intermediates and a process to produce the novel derivatives.The acyl derivatives have pharmacological activity as antibacterial agents.Type: GrantFiled: July 30, 1982Date of Patent: November 13, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Andre Furlenmeier, Paul Lanz
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Patent number: 4481142Abstract: There is presented compounds of the formula ##STR1## wherein A is selected from the group consisting of ##STR2## R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, lower alkyl, the group NR.sub.4 R.sub.5, the group --CH.sub.2 --CO--R.sub.7, the group--NH(CH.sub.2).sub.m NR.sub.8 R.sub.9, hydroxy, lower alkoxy, mercapto and lower alkyl mercapto; R.sub.2 is selected from the group consisting of hydrogen, amino and dilower alkyl amino; R.sub.3 is selected from the group consisting of hydrogen, lower acyloxy and hydroxy; X is selected from the group consisting of hydrogen, halogen, trifluoromethyl, ethyl, .alpha.-hydroxy ethyl and acetyl; Y is hydrogen or halogen; R.sub.4 and R.sub.5 are hydrogen or lower alkyl or together with their co-bonded nitrogen atom form a five to seven membered heterocyclic group; R.sub.7 is selected from the group consisting of hydroxy lower alkoxy and NR.sub.8 R.sub.9 ; R.sub.8 and R.sub.Type: GrantFiled: October 27, 1982Date of Patent: November 6, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Norman W. Gilman, Eugene J. Trybulski, Armin Walser
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Patent number: 4474777Abstract: There are presented novel pharmaceutically active substances which inhibit the intestinal resorption of cholesterol and which accordingly can be used in the control or prevention of atherosclerosis. These active substances are benzodiazepines of the formula ##STR1## wherein R.sup.1 is (C.sub.1 -C.sub.4)-alkyl, R.sup.2 is hydrogen or methyl, R.sup.3 and R.sup.4 each are halogen and R.sup.5 is (C.sub.3 -C.sub.9)-alkylamino substituted by at least two hydroxy groups, (C.sub.3 -C.sub.6)-cycloalkylamino substituted by at least one hydroxy group, glucosamino, galactosamino, mannosamino, monohydroxy-1-azetidinyl, mono- or dihydroxy-1-pyrrolidinyl or mono-, di- or trihydroxy-1-piperidinyl,and the readily hydrolyzable esters and ethers thereof, as well as pharmaceutically acceptable salts of these compounds.Type: GrantFiled: December 17, 1982Date of Patent: October 2, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Jean-Marie Cassal, Albert E. Fischli, Andre Szente
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Patent number: 4472571Abstract: There is presented the compounds 4-deoxy-aclacinomycin A and B and pharmaceutical preparations containing the same. The preparations are effective against bacteria and tumours. Also presented is a process for the preparation of optically active anthracycline glycosides A and B with the 7S-configuration starting from racemic anthracyclinones.Type: GrantFiled: June 30, 1983Date of Patent: September 18, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Akiko Fujiwara, Tatsuo Hoshino
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Patent number: 4472435Abstract: There is presented novel benzophenone derivatives of the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkyl, R.sup.2 is hydrogen or aminoacetyl, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is hydrogen or halogen, R.sup.5 is hydrogen, amino, nitro or a group of the formula R.sup.3 --ON.dbd.C(R.sup.6)--and R.sup.6 is lower alkyl, with the proviso that R.sup.5 is a group of the formula H--ON.dbd.C(R.sup.6)--when R.sup.2 and R.sup.3 are both hydrogen, and their pharmaceutically acceptable acid addition salts.The compounds exhibit aldosterone-antagonistic properties and are accordingly suitable for the control or prevention of heart failure, hepatic ascites, primary aldosteronism and idiopathic hypertension.Type: GrantFiled: July 15, 1981Date of Patent: September 18, 1984Assignee: Hoffman-La Roche Inc.Inventors: Quirico Branca, Albert E. Fischli, Andre Szente
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Patent number: 4469633Abstract: Compounds of the formula ##STR1## wherein X and Y are selected from the group consisting of hydrogen, halogen and trifluoromethyl, are disclosed.The compounds are useful as intermediates in the production of 2-benzazepines, compounds of pharmacological activity.Also disclosed are other intermediates and processes for their production.Type: GrantFiled: November 23, 1981Date of Patent: September 4, 1984Assignee: Hoffmann-La Roche Inc.Inventor: Eugene J. Trybulski
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Patent number: 4464300Abstract: There are presented benzazepines of the formula ##STR1## wherein either R.sup.1 is hydrogen, lower alkyl, 4-pyridyl or the group --(CH.sub.2).sub.n --NR.sup.6 R.sup.7 and R.sup.2 and R.sup.3 together are an additional bond or R.sup.1 and R.sup.2 together are the oxo group and R.sup.3 is hydrogen or lower alkyl, R.sup.4 is phenyl, o-halophenyl or 2-pyridyl, R.sup.5 is halogen or nitro and either R.sup.6 is hydrogen or lower alkyl and R.sup.7 is hydrogen, lower alkyl, lower alkenyl or lower alkynyl or R.sup.6 and R.sup.7 together with the nitrogen atom are 4-(lower alkyl)-1-piperazinyl or 4-morpholinyl and n is the number 0 or 1, and their pharmaceutically acceptable acid additions salts.The compounds possess interesting psychotropic properties, i.e., pronounced anxiolytic properties have been established in the case of certain representative members of this class of substance.Type: GrantFiled: July 15, 1982Date of Patent: August 7, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Rene Borer, Max Gerecke, Emilio Kyburz
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Patent number: 4461906Abstract: 1-Substituted-2-pyrrolidinones of the formula ##STR1## wherein one of R.sup.1, R.sup.2 and R.sup.3 represents hydroxy and the remaining substituents represent hydrogen,are capable of counteracting cerebral insufficiency produced experimentally in animal tests. They can be used therapeutically in the control or prevention of cerebral insufficiency or in the improvement of intellectual capacity. They can be manufactured from novel intermediates and can be processed to provide medicaments.Type: GrantFiled: July 28, 1980Date of Patent: July 24, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Werner Aschwanden, Emilio Kyburz
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Patent number: 4460781Abstract: There are presented compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or lower alkyl; R.sub.6 is halo and R.sub.5 is hydrogen or halo; and compounds of the formulas ##STR2## wherein R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids, hydroxy C.sub.2 to C.sub.7 alkyl, C.sub.2 to C.sub.7 carboxylic acid esters and amides and the group COR.sub.11 wherein R.sub.11 and is selected from the group consisting of alkoxy, amino or mono-lower alkyl amino; R.sub.35 is hydrogen or lower alkyl; R.sub.5 is hydrogen or halo; and R.sub.7 is methyl or chloromethyl, all of which are useful in the preparation of pyrazolobenzazepines.Type: GrantFiled: January 5, 1983Date of Patent: July 17, 1984Assignee: Hoffmann-La Roche Inc.Inventors: George F. Field, Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
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Patent number: 4458072Abstract: There are presented compounds of the formula ##STR1## wherein R.sup.1 is one of the 3-substituents usable in cephalosporin chemistry, R.sup.2 is hydrogen, lower alkyl or COOR.sup.3 -lower alkyl, wherein R.sup.3 is hydrogen, a cation of a base or a readily hydrolyzable ester group, and X is sulphur, oxygen or one of the groups --SO-- and --SO.sub.2 --, and the readily hydrolyzable esters, readily hydrolyzable ethers and salts of these compounds and hydrates of the compounds of formula I or of their esters, ethers and salts, also presented are methods for the manufacture of these compounds as well as compounds used in their manufacture.Type: GrantFiled: September 28, 1981Date of Patent: July 3, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Roland Reiner, Urs Weiss
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Patent number: 4452782Abstract: A pentadecapeptide and salts thereof with immunopotentiating activity is presented. Also presented is a fermentation process for the preparation of the pentadecapeptide by a microorganism of the genus Streptoverticillium and pharmaceutical preparations containing the peptide or its salts.Type: GrantFiled: August 26, 1982Date of Patent: June 5, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Kenji Takemoto, Yumiko Miyasaka, Hideo Ishitsuka, Yasuji Suhara, Hiromi Maruyama
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Patent number: 4447533Abstract: There is presented an antibiotic compound of the formula ##STR1## and the pharmaceutically acceptable salts and esters thereof. The compound exhibits activity as an anti-swine dysentery agent and an antimicrobial agent.Also presented is a fermentation process to produce the compound of formula I.Type: GrantFiled: July 30, 1982Date of Patent: May 8, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Chao-Min Liu, Homer D. Tresner, John Westley
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Patent number: 4440685Abstract: Novel Imidazobenzodiazepines and their analogs are useful as anticonvulsants, muscle relaxant, anxiolytic and sedative agents. Preferred compounds of this class belong to the imidazo[1,5-a] [1,4] diazepine series which may have a very wide variety of organic substituents. An especially preferred genus included with the purview of the invention encompasses a compound of the formula ##STR1## wherein R.sub.1 is hydrogen and lower alkyl, preferably methyl; R.sub.3 and R.sub.5 are hydrogen; R.sub.4 is hydrogen, nitro or halogen, most preferably, chlorine, and in a most preferred embodiment when positioned on the fused benzo portion of the imidazobenzodiazepine is in the 8-position thereof; R.sub.6 is phenyl or halo, nitro, or lower alkyl-substituted phenyl, preferably, halo, with fluorine being the preferred halogen, the substituted fluoro being positioned in the 2-position of the phenyl moiety; and R.sub.2 is hydrogen and lower alkyl.Type: GrantFiled: June 16, 1983Date of Patent: April 3, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Armin Walser, Rodney I. Fryer
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Patent number: 4436662Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sub.1 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, hydroxy, lower alkoxy or acyloxy and R.sub.2 and R.sub.4 are hydrogen or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 taken together are oxo groups with the proviso that at least one oxo group is present; R is selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids and the esters and amides thereof, hydroxy C.sub.2 to C.sub.7 alkyl and amino C.sub.2 to C.sub.7 alkyl or mono- or di-lower alkyl amino C.sub.2 to C.sub.7 alkyl; R.sub.5 is halogen or hydrogen; and R.sub.6 is halogen with the proviso that when R.sub.1 or R.sub.3 is hydroxy, lower alkoxy or acyloxy, then R is lower alkyl or hydrogen and the N-oxides and the pharmaceutically acceptable salts thereof.Type: GrantFiled: March 31, 1983Date of Patent: March 13, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
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Patent number: 4431804Abstract: There is provided cephalosporin derivatives of the formula ##STR1## in which R.sup.1 is carboxy-lower alkyl andR.sup.2 is hydrogen, a cation or (with the oxygen atom) a readily hydrolyzable ether group,as well as readily hydrolyzable esters and salts of these compounds and hydrates of the compounds of formula I and of their esters and salts. Also provided are methods for their manufacture and pharmaceutical preparations containing the compounds of formula I.Type: GrantFiled: January 29, 1982Date of Patent: February 14, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Peter Angehrn, Roland Reiner