Additional Hetero Ring Containing Patents (Class 544/96)
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Patent number: 4501874Abstract: This invention is novel compounds containing one or more 2,3-epoxyalkyl carbamate moieties wherein the carbamate nitrogen is tertiary; prepared by a process which comprises(A) contacting an epihalohydrin carbonate with a secondary amine-containing compound wherein the secondary amine has a pKa of between 6 and 12, in a polar organic solvent under conditions such that a 3-halo-2-hydroxyalkyl carbamate wherein the carbamate nitrogen is tertiary is prepared; and(B) contacting the 3-halo-2-hydroxyalkyl carbamate with an alkali metal hydroxide, alkaline earth metal hydroxide, a secondary amine with a pH of 8 or grater, or an ion-exchange resin with pendant moieties containing hydroxide moieties or a secondary amine moiety with a pH of 8 or greater, in a lower alkanol solvent under conditions such that the 3-halo-2-hydroxy moieties are converted to 2,3-epoxyalkyl moieties so as to prepare a 2,3-epoxyalkyl carbamate.Type: GrantFiled: May 2, 1984Date of Patent: February 26, 1985Assignee: The Dow Chemical CompanyInventor: Joseph W. Hanafin
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Patent number: 4495355Abstract: A novel optically active diamide derivative represented by the following general formula is provided, which is useful as a starting material for asymmetric synthesis of optically active compounds, ##STR1## wherein R.sup.1 is an acyclic or cyclic, divalent atomic group containing at least one carbon atom which will, upon substitution of one of the heterocyclic groups in the formula with a nucleophilic reagent, stand as an asymmetric center in the substitution product; R.sup.2 is a substituent which has such a configuration and a molecular size that the regioselectivity in the substitution reaction of the heterocyclic group with the nucleophilic reagent can be determined by a stereo-chemical interaction thereof with the substituent R.sup.1, the steric configuration of the two asymmetric carbon atoms to which the R.sup.2 substituents are attached being identical; X is a sulfur atom or an oxygen atom; and n is an integer which is 1 or 2.Type: GrantFiled: December 9, 1982Date of Patent: January 22, 1985Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Eiichi Fujita, Yoshimitsu Nagao, Takao Ikeda, Takehisa Inoue
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Patent number: 4495349Abstract: This invention relates to the use of 6-aryluracils as antiinflammatory and antiarthritic agents and also to both novel intermediates and novel processes for the preparation of selected 6-aryluracils.Type: GrantFiled: July 11, 1983Date of Patent: January 22, 1985Assignee: The Upjohn CompanyInventors: Harvey I. Skulnick, Herman W. Smith, Robert J. Smith, Wendell Wierenga
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Patent number: 4468395Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is a prostaglandin or prostacyclin residue;Y is oxygen, sulfur, imino, or N-(C.sub.1 -C.sub.4 -alkyl) imino;Q is (CR.sub.6 R.sub.7).sub.p wherein p is an integer of 0 to 3;R.sub.2 is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; C.sub.1 -C.sub.4 -alkoxycarbonyl; benzyloxycarbonyl; cyano; or di-C.sub.1 -C.sub.4 -alkylaminocarbonyl;R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 each independently is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; or aryl; andR.sub.3 and R.sub.4 together form a trimethylene, tetramethylene, or 1,3-butadienylene group when R.sub.2 and R.sub.5 together represent a direct bond;have valuable pharmacological properties, e.g., as blood-pressure-lowering or abortive agents.Type: GrantFiled: May 20, 1982Date of Patent: August 28, 1984Assignee: Schering, AktiengesellschaftInventors: VorbruHelmut, Walter Elger, Michael-Harold Town, Ekkehard Schillinger
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Patent number: 4448963Abstract: A 1-(4-aminobenzyl)-2,3-dioxopiperazine derivative represented by the formula: ##STR1## and an acid addition salt thereof have excellent carcinostatic activity but a low toxicity. Therefore, said compounds are useful as medicines and also as intermediates.Type: GrantFiled: February 22, 1982Date of Patent: May 15, 1984Assignee: Toyama Chemical Co., Ltd.Inventors: Takako Hori, Chosaku Yoshida, Yasuo Kiba, Ryuko Takeno, Joji Nakano, Jun Nitta, Sumiko Kishimoto, Shohachi Murakami, Hisatsugu Tsuda, Isamu Saikawa
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Patent number: 4434295Abstract: The present specification provides novel analogs of khellin. These analogs are all useful as antiatherosclerotic agents. Particularly, the present specification provides 4-methoxy, 9-methoxy, or 4,9-dimethoxy-6,7-dihydro-7,7-disubstituted-5H-furo[3,2-g][1]benzopyran-5- ones.Type: GrantFiled: May 17, 1982Date of Patent: February 28, 1984Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
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Patent number: 4414213Abstract: A series of 1,4-dihydropyrid-5-yl cyclic imidate esters have been prepared possessing the general formula ##STR1## wherein R and R.sup.1 are independently selected from hydrogen, lower alkyl or alkoxyalkyl groups; R.sup.2 is lower alkyl, aryl, or hetaryl; R.sup.3 is cycloalkyl, aryl or hetaryl, generally with electron-withdrawing substituents; R.sup.4 is lower alkyl, alkoxyalkyl, aminoalkyl, haloalkyl, or dialkylaminoalkyl; R.sup.5 is lower alkyl or aryl; m is 0 or 1; and n is 0, 1, or 2. Compounds of this series demonstrate blockage of calcium ion flux in tissue preparations in vitro and vasodilation in animal testing in vivo.Type: GrantFiled: March 22, 1982Date of Patent: November 8, 1983Assignee: Mead Johnson & CompanyInventors: Graham S. Poindexter, David L. Temple, Jr.
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Patent number: 4414211Abstract: 5-Membered, 6-membered and 7-membered heterocyclic derivatives of guanidine having hypoglycemic activity.Type: GrantFiled: March 14, 1980Date of Patent: November 8, 1983Assignee: McNeilab, Inc.Inventor: Chris R. Rasmussen
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Patent number: 4409224Abstract: Pyrimido[1,6-a]indole derivatives characterized by having a substituted ethyl group at position 5 and optionally being further substituted at various positions on the pyrimido[1,6-a]indole nucleus are disclosed. The foregoing compounds are useful as antihypertensive agents in a mammal. Methods for their preparation also are disclosed.Type: GrantFiled: July 13, 1981Date of Patent: October 11, 1983Assignee: American Home Products Corp.Inventor: Ivo L. Jirkovsky
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Patent number: 4391814Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is the residue of an antiphlogistically effective carboxylic acid of the formula R.sub.1 COOH,n is an integer 1, 2, or 3, andX is oxygen, sulfur, or optionally alkylated nitrogenhave valuable antiinflammatory activity.Type: GrantFiled: December 23, 1981Date of Patent: July 5, 1983Assignee: Schering AktiengesellschaftInventor: Helmut Vorbruggen
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Patent number: 4378357Abstract: This invention relates to novel heterocyclic fungicides which are effective in controlling a broad spectrum of phytopathogenic fungi found in the four main classes of fungi namely Phycomycetes, Ascomycetes, Fungi Imperfecti, and Basidiomycetes. Certain of these compounds are especially effective in controlling sclerotial forming fungi such as Whetzelinia sclerotiorum=(Sclerotinia sclerotiorium) and Botrytis cinerea.Type: GrantFiled: December 16, 1977Date of Patent: March 29, 1983Assignee: Rohm and Haas CompanyInventors: George A. Miller, Lendon N. Pridgen
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Patent number: 4373102Abstract: Novel dyes of the formula ##STR1## where A is cyano, carbo-C.sub.1 -C.sub.4 -alkoxy, carbamyl, N-C.sub.1 -C.sub.4 -alkylcarbamyl, N-phenylcarbamyl, acetyl, benzoyl, 4-nitrophenyl or 4-cyanophenyl,X is hydrogen, chlorine, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, and if n is 2 the substituents may be identical or different,n is 1 or 2,R.sup.1 is hydrogen, methyl, ethyl or 2-hydroxyethyl andR.sup.2 is phenyl or cyclohexyl, orR.sup.1 is hydrogen andR.sup.2 is C.sub.1 -C.sub.4 -alkyl, orR.sup.1 and R.sup.2 are C.sub.1 -C.sub.6 -alkyl, allyl or phenyl-C.sub.1 -C.sub.4 -alkyl orthe group ##STR2## is a saturated heterocyclic five-membered or six-membered ring which may additionally contain an oxygen or a further nitrogen as ring members,Y is hydrogen, hydroxyl, methyl or ethyl; ##STR3## where R.sup.3 is linear or branched C.sub.1 -C.sub.12 -alkyl, or is phenyl; ##STR4## where R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.5 is hydrogen, linear or branched C.sub.1 -C.sub.Type: GrantFiled: March 7, 1980Date of Patent: February 8, 1983Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Wolfgang Elser, Gustav Bock, Wolf-Dieter Kermer
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Patent number: 4356024Abstract: A process for the preparation of a 1-amino-1,3,5-triazine-2,4(1H, 3H)-dione compounds comprising the steps of reacting an N-substituted imido-dicarboxylic acid diaryl ester with an isothiosemicarbazone at a temperature of between 50.degree. and 150.degree. C. to form a 1-alkylidene-amino-1,3,5-triazine-2,4(1H, 3H)-dione reaction product; and thereafter, hydrolyzing the reaction product in an acid medium. The reaction product need not be separated from the reaction mixture before the hydrolysis step. Certain novel 1-amino-1,3,5-triazine-2,4(1H, 3H)-dione compounds are provided. The compounds are useful as herbicides.Type: GrantFiled: February 10, 1981Date of Patent: October 26, 1982Assignee: Bayer AktiengesellschaftInventors: Karlfried Dickore', Engelbert Kuhle
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Patent number: 4346088Abstract: Thiazoline derivatives of the general formula I ##STR1## wherein R.sup.1 to R.sup.7 have the specified meanings, physiologically acceptable acid addition salts thereof, processes for their preparation, pharmaceutical preparations based on these compounds and their use for acting on the serum lipoprotein spectrum. The invention moreover relates to compounds of the formulae ##STR2## wherein A, R, R.sup.1 to R.sup.7, Y and Z have the specified meanings.Type: GrantFiled: July 1, 1980Date of Patent: August 24, 1982Assignee: Hoechst AktiengesellschaftInventors: Hans-Jochen Lang, Bernhard Seuring, Ernold Granzer
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Patent number: 4333936Abstract: 5-Benzyl-4-amino-pyrimidine-2-amidines which may or may not be substituted in the phenyl ring, and their physiologically acceptable addition salts with acids, processes for their preparation, drugs containing these compounds, and their use in infectious diseases.Type: GrantFiled: July 3, 1978Date of Patent: June 8, 1982Assignee: BASF AktiengesellschaftInventors: Peter Scharwaechter, Klaus Gutsche, Wilhelm Kohlmann, Gerhard Kroemer, deceased, by Norma Kroemer, legal representative, by Helmut Kroemer, legal representative, by Maria M. Kroemer, legal representative
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Patent number: 4324792Abstract: The present invention provides compounds of the general formula (I) ##STR1## and physiologically acceptable salts and bioprecursors thereof in which ##STR2## represents either ##STR3## R.sup.1 represents hydrogen, halogen, C.sub.1-4 alkoxy, hydroxy, alkyl, R.sup.4 CH(OH)--, cyano or R.sup.5 CONH--, R.sup.2 and R.sup.3, which may be the same or different, each represents a straight or branched chain alkyl group or alkenyl group or R.sup.2 and R.sup.3 may, together with the nitrogen atom to which they are attached, form a saturated heterocyclic ring containing from 5 to 7 members which may optionally contain an oxygen atom; R.sup.4 represents hydrogen or alkyl; and R.sup.5 represents hydrogen, alkyl or C.sub.1-4 alkoxy. The compounds have been shown to exhibit H.sub.1 -antagonist activity in standard pharmacological tests.Type: GrantFiled: October 3, 1980Date of Patent: April 13, 1982Assignee: Glaxo Group LimitedInventors: John Bradshaw, Alexander W. Oxford, David I. C. Scopes
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Patent number: 4315019Abstract: This invention relates to novel substituted aryl lower alkamine and more precisely to arylmethylamine, the methyl group of which is substituted with one more polyfluoromethyl radicals.This invention also relates to the process for producing said compounds.The resulting compounds have pharmacological utility and may be used as a drug in human and veterinary medicine.Type: GrantFiled: August 18, 1980Date of Patent: February 9, 1982Assignee: Science Union et CieInventors: Charles Malen, Pierre Roger, Michel Laubie
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Patent number: 4308266Abstract: The present invention provides tetraline derivatives, useful for the treatment of hypertension, a process for their preparation and compositions containing these compounds.Type: GrantFiled: September 7, 1979Date of Patent: December 29, 1981Assignee: Sandoz Ltd.Inventor: Max-Peter Seiler
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Patent number: 4307234Abstract: Pyrimido[1,6-a]indole derivatives characterized by having a substituted ethyl group at position 5 and optionally being further substituted at various positions on the pyrimido[1,6-a]indole nucleus are disclosed. The foregoing compounds are useful as antihypertensive agents in a mammal. Methods for their preparation also are disclosed.Type: GrantFiled: September 11, 1978Date of Patent: December 22, 1981Assignee: American Home Products Corp.Inventor: Ivo L. Jirkovsky
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Patent number: 4307237Abstract: This invention is directed toward pharmacologically active compound of the formula ##STR1## wherein A is ##STR2## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, phenyl, alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, substituted amino lower alkyl, substituted phenyl, pyridyl, aralkyl and the groups ##STR3## wherein R is hydrogen or lower alkyl and ROOC where R is lower alkyl; R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, acyloxy lower alkyl, alkoxy lower alkyl, halo lower alkyl, amino or substituted amino lower alkyl, amino, cyano, cyano lower alkyl, substituted amino, chloro, bromo and iodo, the group --COOR where R is hydrogen or lower alkyl, the group ##STR4## where R is hydrogen or lower alkyl, or derivatives thereof, e.g., the group R--C.dbd.Type: GrantFiled: August 14, 1980Date of Patent: December 22, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Armin Walser, Rodney I. Fryer
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Patent number: 4289765Abstract: 4-Aminopyridines of the formula ##STR1## in which R.sup.1 is hydrogen or alkyl of up to 6 carbon atoms andR.sup.2 represents (a) alkyl of up to 6 carbon atoms substituted up to three times with at least one radical from the group of halogen and hydroxyl, with formyl acetalized with an alcohol of up to 3 carbon atoms, alkylthio of up to 3 carbon atoms, phenylthio or the corresponding alkyl- and phenyl-sulfoxy and sulfone groups, the phenyl ring optionally carrying in each case up to three substituents from the group of alkyl, alkyl halide, alkoxy, mono- or dialkylamino having each up to 4 carbon atoms in each alkyl radical, halogen, nitro, amino and hydroxy, or (b) phenylalkyl or diphenyl-alkyl of up to 6 carbon atoms in the linear or branched alkyl moiety, the phenyl rings optionally being substituted up to three times with at least one radical from the group of alkyl, alkoxy, alkyl halide with up to 4 carbon atoms each, halogen, amino, hydroxy, nitro, the sulfamoyl group and the methylene dioxy radical, orR.Type: GrantFiled: January 7, 1980Date of Patent: September 15, 1981Assignee: Hoechst AktiengesellschaftInventors: Wilfried Greve, Heinzgeorg von Schuh, Hiristo Anagnostopulos
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Patent number: 4288437Abstract: Compounds of the formula ##STR1## wherein Ar is phenyl; mono- or di-substituted phenyl, where the substituents are one to two halogens, one to two alkyls of 1 to 3 carbon atoms, or one amino, nitro, cyano or trifluoromethyl; or pyridinyl;R is hydrogen, chlorine, methyl or methoxy;R.sub.1 is hydrogen or methyl;R.sub.2 is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, methyl-(cycloalkyl of 3 to 8 carbon atoms) or --A--R.sub.4,where A is alkylene of 2 to 3 carbon atoms, and R.sub.4 is hydroxyl, methylamino, dimethylamino, N-methyl-ethylamino, diethylamino, pyrrolidino, piperidino, hexamethyleneimino, morpholino or 4-methyl-1-piperazinyl; orR.sub.1 and R.sub.Type: GrantFiled: July 28, 1980Date of Patent: September 8, 1981Assignee: Boehringer Ingelheim GmbHInventors: Wolfhard Engel, Gunter Trummlitz, Ernst Seeger, Joachim Kahling
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Patent number: 4288443Abstract: The invention relates to compounds of the general formula ##STR1## and physiologically acceptable salts and N-oxides, hydrates and bioprecursors thereof, in which R.sub.1 and R.sub.2 which may be the same or different each represent hydrogen, C.sub.1-8 alkyl, C.sub.4-8 cycloalkyl, C.sub.3-6 alkenyl, aralkyl with 1 to 4 carbon atoms in the alkyl residue or C.sub.1-8 alkyl interrupted by an oxygen atom or a group ##STR2## in which R.sub.5 represents hydrogen or C.sub.1-8 alkyl, or R.sub.1 and R.sub.2 may together with the nitrogen atom to which they are attached, form a saturated monocyclic 5 to 7 membered heterocyclic ring which may additionally contain the heterofunction O or ##STR3## R.sub.3 represents straight or branched chain C.sub.1-8 alkyl, alkoxyalkyl with 1 to 8 carbon atoms in each alkyl residue, C.sub.1-8 hydroxyalkyl, C.sub.1-8 alkoxycarbonyl, alkyl thioalkyl with 1 to 8 carbon atoms in each alkyl residue, halogen or aryl;R.sub.4 represents hydrogen, C.sub.1-8 alkyl, C.sub.Type: GrantFiled: February 25, 1980Date of Patent: September 8, 1981Assignee: Glaxo Group LimitedInventors: Duncan B. Judd, John W. Clitherow, Barry J. Price, John Bradshaw
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Patent number: 4284569Abstract: The present specification relates to the antiatherosclerotic use of khellin and related furochromones, and further provides novel antiatherogenic furochromones.Type: GrantFiled: January 28, 1980Date of Patent: August 18, 1981Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
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Patent number: 4279905Abstract: Novel, 3-amino-1-benzoxepin-5 (2H)-one derivatives and methods for their production are disclosed. These derivatives correspond to the Formula I: ##STR1## wherein: R.sub.1 and R.sub.2 independently of one another arehydrogen,C.sub.1 -C.sub.5 alkyl,C.sub.1 -C.sub.5 alkyl substituted with a terminal phenyl, or a phenyl containing one or two halogens, methyl or methoxy groups, a 3,4-methylenedioxy or a 3,4-ethylenedioxy group,C.sub.2 -C.sub.5 alkyl substituted with terminal hydroxy or methoxy or,C.sub.3 -C.sub.4 alkenyl; orone of R.sub.1 and R.sub.2 are hydrogen or a C.sub.1 -C.sub.5 alkyl and the other is a C.sub.2 -C.sub.5 alkyl substituted with a terminal NR.sub.5 R.sub.6 ;R.sub.5 and R.sub.6 independently of one another are hydrogen or C.sub.1 -C.sub.5 alkyl; orR.sub.5 and R.sub.6 are together a 5 to 7 member ring, orR.sub.5 and R.sub.6 are together a 5 to 7 member ring having heterogeneous oxygen, sulfur or nitrogen;R.sub.1 and R.sub.2 are together a 5 to 7 member ring, orR.sub.1 and R.sub.Type: GrantFiled: July 28, 1980Date of Patent: July 21, 1981Assignee: Kali-Chemie Pharma GmbHInventors: Heinrich-Wilhelm Ohlendorf, Klaus-Ullrich Wolf, Wilhelm Kaupmann
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Patent number: 4279902Abstract: Acetamide derivatives are provided having the structure ##STR1## wherein X is a single bond, --CH.sub.2 -- or --O--, R.sup.1 and R.sup.2 may be the same or different and are lower alkyl, phenyl-lower alkoxy-lower alkyl, lower alkenyl, phenyl-lower alkyl or lower alkoxy, or ##STR2## may be taken together to form a 5- to 7-membered heterocyclic ring optionally containing one other hetero atom, such as nitrogen, sulfur or oxygen; Y is hydroxyl, OR wherein R is lower alkyl, lower alkenyl or lower alkanoyl, or ##STR3## wherein R.sup.1 and R.sup.2, and R.sup.1 and R.sup.2 taken together with the nitrogen to which they are attached are as defined above, and n is 1 to 6.These compounds are useful as anti-arrhythmia agents and have been found to be effective in the treatment of acute myocardial infarction.Type: GrantFiled: August 6, 1980Date of Patent: July 21, 1981Assignee: E. R. Squibb & Sons, Inc.Inventors: Frederic P. Hauck, Glenn A. Jacobs
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Patent number: 4279904Abstract: Novel 3-amino-1-benzoxepine derivatives and methods for their production are disclosed. These derivatives correspond to the Formula I ##STR1## wherein: R.sub.1 and R.sub.2 independently of one another arehydrogen,C.sub.1 -C.sub.5 alkyl,C.sub.1 -C.sub.5 alkyl substituted with a terminal phenyl, or a phenyl containing one or two halogens, methyl or methoxy groups, a 3,4-methylenedioxy or a 3,4-ethylenedioxy group,C.sub.2 -C.sub.5 alkyl substituted with terminal hydroxy or methoxy or,C.sub.3 -C.sub.4 alkenyl; orone of R.sub.1 and R.sub.2 are hydrogen or a C.sub.1 -C.sub.5 alkyl and the other is a C.sub.2 -C.sub.5 alkyl substituted with a terminal NR.sub.7 R.sub.8 ;R.sub.7 and R.sub.8 independently of one another are hydrogen or C.sub.1 -C.sub.5 alkyl; orR.sub.7 and R.sub.8 are together a 5 to 7 member ring or said ring having heterogeneous oxygen, sulfur or nitrogen, orR.sub.1 and R.sub.2 are together a 5 to 7 member ring or said ring having heterogeneous oxygen, sulfur or NR.sub.9 ;R.sub.Type: GrantFiled: July 28, 1980Date of Patent: July 21, 1981Assignee: Kali-Chemie Pharma GmbHInventors: Heinrich-Wilhelm Ohlendorf, Klaus-Ullrich Wolf, Wilhelm Kaupmann, Henning Heinemann
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Patent number: 4275209Abstract: The present invention relates to novel thioxanthene and xanthene derivatives which have useful pharmacodynamic activity, such as neuroleptic activity and antiemetic activity, methods for the preparation of said derivatives, pharmaceutical compositions containing same, and a method for the treatment of psychic disorders by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.Type: GrantFiled: December 21, 1979Date of Patent: June 23, 1981Assignee: Kefalas A/SInventors: Niels Lassen, Klaus P. Bogeso, Peter B. Hansen, Jorn L. M. Buus, Allan J. Bigler
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Patent number: 4267345Abstract: Certain arylmethyl amines have been prepared wherein the "methyl" carbon is substituted with a polyfluoroalkyl radical. The compounds form acid addition salts, exist in resolvable stereoisomeric forms, and are useful for treating hypertension. Formulations for human and veterinary medicine are described, as well as methods of use.Type: GrantFiled: April 19, 1979Date of Patent: May 12, 1981Assignee: Science Union et CieInventors: Charles E. Malen, Pierre Roger, Michel Laubie
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Patent number: 4259259Abstract: Covers a process for the preparation of a .beta.-aminopropionanide of the formula ##STR1## wherein R.sub.1 is H or methyl, n is an integer of 2 to 6 and R.sub.2 and R.sub.3, taken singly are hydrogen or lower alkyl groups containing 1 to 4 carbon atoms or R.sub.2 and R.sub.3, taken jointly are combined with the nitrogen atom to form a heterocyclic group selected from the groups consisting of morpholine, pyrrolidine and piperidine ring groups; which process comprises reacting in the presence of an alkali or alkaline earth metal salt of a strong acid having a pK.sub.a of less than about 2.0 acting as a catalyst a tertiaryaminoalkyl amine of the formula: where R.sub.2, R.sub.3 and n are as above with an acrylic or methacrylic compound of the formula: ##STR2## where R.sub.1 is as above and R.sub.4 is lower alkyl and recovering said .beta.-aminopropionamide.Type: GrantFiled: November 15, 1979Date of Patent: March 31, 1981Assignee: Texaco Development Corp.Inventor: Edward E. McEntire
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Patent number: 4258181Abstract: This disclosure describes anthracene-9,10-bis-carbonyl-hydrazones and derivatives thereof useful as antibacterial agents, for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers.Type: GrantFiled: May 7, 1979Date of Patent: March 24, 1981Assignee: American Cyanamid CompanyInventors: Keith C. Murdock, Frederick E. Durr
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Patent number: 4256666Abstract: Covers a process for the preparation of a .beta.-aminopropionamide of the formula ##STR1## wherein R.sub.1 is H or methyl, n is an integer of 2 to 6 and R.sub.2 and R.sub.3, taken singly are hydrogen or lower alkyl groups containing 1 to 4 carbon atoms or R.sub.2 and R.sub.3, taken jointly are combined with the nitrogen atom to form a heterocyclic group selected from the groups consisting of morpholine, pyrrolidine and piperidine ring groups; which process comprises reacting in the presence of a Lanthanide salt having an anion derivative from a strong acid having a pK.sub.a of about 5 or less acting as a catalyst, a tertiaryaminoalkyl amine of the formula: ##STR2## where R.sub.2, R.sub.3 and n are as above with an acrylic or methacrylic compound of the formula: ##STR3## where R.sub.1 is as above and R.sub.4 is lower alkyl and recovering said .beta.-aminopropionamide.Type: GrantFiled: October 29, 1979Date of Patent: March 17, 1981Assignee: Texaco Development CorporationInventor: Edward E. McEntire
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Patent number: 4256665Abstract: Covers a process for the preparation of a .beta.-aminopropionamide of the formula ##STR1## wherein R.sub.1 is H or methyl, n is an integer of 2 to 6 and R.sub.2 and R.sub.3, taken singly are hydrogen or lower alkyl groups containing 1 to 4 carbon atoms or R.sub.2 and R.sub.3, taken jointly are combined with the nitrogen atom to form a heterocyclic group selected from the groups consisting of morpholine, pyrrollidine and piperidine ring groups; which process comprises reacting in the presence of carbon dioxide acting as a catalyst a tertiaryaminoalkyl amine of the formula. ##STR2## where R.sub.2, R.sub.3 and n are as above with an acrylic or methacrylic compound of the formula: ##STR3## where R.sub.1 is as above and R.sub.4 is lower alkyl and recovering said .beta.-aminopropionamide.Type: GrantFiled: August 31, 1979Date of Patent: March 17, 1981Assignee: Texaco Development CorporationInventor: Edward E. McEntire
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Patent number: 4251461Abstract: A non-catalytic process for the preparation of N-(tertiaryaminoalkyl)acrylamides is disclosed which comprises subjecting a corresponding .beta.-aminopropionamide to a pyrolysis temperature of about 180.degree. to 300.degree. C. after storage of the .beta.-aminopropionamide in an atmospheric holding tank at a temperature of about 150.degree. to 220.degree. C. from eight to seventy-two hours prior to pyrolysis. The corresponding .beta.-aminopropionamide compounds can be prepared by mixing and reacting at least two moles of a tertiaryaminoalkyl amine with an acrylic acid or ester compound. The inventive process provides the production of the N-(tertiaryaminoalkyl)acrylamides in high yields with minimal back addition or polymerization and greatly reduced acid impurity levels.Type: GrantFiled: January 17, 1980Date of Patent: February 17, 1981Assignee: Texaco Development CorporationInventor: David R. Livingston
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Patent number: 4250173Abstract: A compound, with hypolgycaemic activity, having formula (II) or a pharmaceutically acceptable quaternary ammonium or acid addition salt thereof: ##STR1## wherein X represents oxygen or sulphur; n.sub.7 represents zero or 1;R.sup.7 represents hydrogen or C.sub.1-6 alkyl;R.sup.1 and R.sup.2 are the same or different and represent hydrogen, C.sub.1-6 alkyl, phenyl, benzyl, or C.sub.3-6 cycloalkyl;R.sup.3 represents hydrogen, C.sub.1-6 alkyl, phenyl or benzyl;R.sup.4 represents hydrogen or C.sub.1-6 alkyl;R.sup.5 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.4 and R.sup.5 together represent the remaining members of a 5- or 6-membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl, carboxy or C.sub.Type: GrantFiled: November 14, 1979Date of Patent: February 10, 1981Assignee: Beecham Group LimitedInventor: Barrie C. C. Cantello
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Patent number: 4247556Abstract: There are prepared 7-azabenzimidazoles of the formula ##STR1## where R.sub.1 and R.sub.2 are the same or different and are hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.6 -alkanol or --NR.sub.1 R.sub.2 is a 5 to 7 membered saturated heterocyclic ring having either one nitrogen atom, one nitrogen atom and one oxygen atom or two nitrogen atoms, R.sub.3 is hydroxy, an amino group, a mono C.sub.1 -C.sub.6 -Alkylamino group, a di-C.sub.1 -C.sub.6 -alkylamino group, or a C.sub.2 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, mercapto, C.sub.1 -C.sub.6 -alkylmercapto, hydroxy or C.sub.1 -C.sub.6 -alkoxy, R.sub.5 is hydrogen or halogen and A is a C.sub.2 -C.sub.6 -alkylene group or a salt of such compound. Preferably R.sub.1 and R.sub.2 are two equal C.sub.1 -C.sub.6 -alkyl groups or --NR.sub.1 R.sub.2 is piperidino, pyrrolidino, morpholino, homopiperidino, piperazino or homopiperazino, R.sub.3 is hydroxy, mercapto, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylmercapto or C.sub.1 -C.sub.Type: GrantFiled: January 15, 1979Date of Patent: January 27, 1981Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Walter von Bebenburg, Istvan Szelenyi, Klaus Thiemer
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Patent number: 4231921Abstract: Novel compounds of the general formula I ##STR1## wherein M.sup.q.sym. is a metal ion carrying a double or triple positive charge and q is 2 or 3 and r is 1 or 2, the quotient q/r being 1, 1.5, 2 or 3, and L is a piperidine which is substituted by at least one enolate group in the 1-position or 4-position and wherein the ring nitrogen is sterically hindered by alkyl substituents in the adjacent positions, and m is 0, 1 or 2 and A is H.sub.2 O or an amine.Type: GrantFiled: July 10, 1978Date of Patent: November 4, 1980Assignee: Ciba-Geigy CorporationInventor: Paul Moser
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Patent number: 4228281Abstract: Dicarboxylic acids containing at least two triazine rings are very suitable for producing thermoplastic polyesters having high glass transition temperatures and high dimensional stability under heat, and at the same time good processing characteristics.Type: GrantFiled: September 18, 1978Date of Patent: October 14, 1980Assignee: Ciba-Geigy CorporationInventors: Thomas Kainmuller, Jurgen Habermeier, Lothar Buxbaum
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Patent number: 4217453Abstract: Disclosed are 6-amido-3-substituted-amino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxyli c acids (I): ##STR1## wherein R.sup.1 is hydrogen or acyl; and R' and R" are independently selected from the group consisting of: hydrogen, substituted and unsubstituted: alkyl and aralkyl, or together form a substituted or unsubstituted cyclic group. Such compounds and their pharmaceutically acceptable salt, 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: GrantFiled: July 24, 1978Date of Patent: August 12, 1980Assignee: Merck & Co., Inc.Inventors: Burton G. Christensen, Ravindra N. Guthikonda, Ronald W. Ratcliffe
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Patent number: 4210655Abstract: Compounds of the class of (2-benzofuranyl)-1,2,3,6-tetrahydropyridines and (2-benzofuranyl)-piperidines which at the ring nitrogen atom are unsubstituted or substituted by a substituent of the class of certain aliphatic, cycloaliphatic and araliphatic radicals, and their pharmaceutically acceptable acid addition salts have valuable pharmacological properties. In particular, they inhibit monoamine oxidase and antagonize the action of tetrabenazine. They are useful as active ingredients for therapeutic compositions for the treatment of mental depression. Specific embodiments are 4-(2-benzofuranyl)-piperidine, 2-(5,6-dimethyl-2-benzofuranyl)-piperidine and their hydrochlorides.Type: GrantFiled: April 5, 1978Date of Patent: July 1, 1980Assignee: Ciba-Geigy CorporationInventors: Karl Schenker, Raymond Bernasconi
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Patent number: 4208327Abstract: 5-Aryl-1-(2-oxazolin-2-yl)-1H-1,4-benzodiazepines and related compounds having the formula ##STR1## wherein A is methylene or carbonyl; Z is oxygen, imino or thio; R.sup.1, R.sup.2, and R.sup.3 independently are hydrogen, halogen, trifluoromethyl or nitro; R.sup.4 is hydrogen or hydroxy; and n is positive integer from 1 to 3 inclusive are disclosed. These compounds are useful because of their central nervous system activity.Type: GrantFiled: April 3, 1979Date of Patent: June 17, 1980Assignee: G. D. Searle & Co.Inventor: Peter K. Yonan
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Patent number: 4154739Abstract: Novel halogeno-benzothiophenecarboxylic acids and a novel process for their preparation by reacting substituted or unsubstituted thiophenols with dihalogenomaleic anhydrides or derivatives thereof are described. The novel halogeno-benzothiophenecarboxylic acids are valuable intermediates for the preparation of pharmaceutical active compounds having an antiallergic action.Type: GrantFiled: February 9, 1978Date of Patent: May 15, 1979Assignee: Ciba-Geigy CorporationInventors: Niklaus Buhler, Hans Bosshard
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Patent number: 4154743Abstract: Novel halogeno-benzofuranone-carboxylic acids and a novel process for their preparation by reacting substituted or unsubstituted phenols with dihalogenomaleic anhydrides or derivatives thereof are described. The novel halogeno-benzofuranone-carboxylic acids are valuable intermediates for the preparation of pharmaceutical active compounds having an antiallergic action or for the preparation of biocidal active compounds for combating plant and animal pests, in particular phytopathogenic fungi and bacteria.Type: GrantFiled: February 9, 1978Date of Patent: May 15, 1979Assignee: Ciba-Geigy CorporationInventors: Hans Bosshard, Niklaus Buhler
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Patent number: 4138545Abstract: Disclosed are polyfunctional oxazolidine-terminated polyesters of the general formula: ##STR1## WHEREIN Z" is the residue of a polyester having a plurality of terminal ##STR2## groups, the polyester being the condensation product of organic acids and alcohols of the formulae ##STR3## AND R.sup.4 (OH).sub.p, in which o is 2 or 3 and p is 2 to 4, each of o and p preferably being 2;R.sup.1 and R.sup.2 are hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl, benzyl, or collectively C.sub.5 -C.sub.6 cycloalkylene, preferably hydrogen;R.sup.3 is a covalent bond, a C.sub.1 -C.sub.10 residue of an aliphatic or aromatic polycarboxylic acid, preferably C.sub.1 -C.sub.10 alkylidene;R.sup.4 is the residue of a polyol having 2-15 carbon atoms, preferably C.sub.2 -C.sub.10 alkylidene;X and Y are selected from the radicals (--CH.sub.2 --).sub.2 and (--CH.sub.2 --).sub.3, preferably (--CH.sub.2 --).sub.Type: GrantFiled: January 4, 1978Date of Patent: February 6, 1979Assignee: Rohm and Haas CompanyInventors: William D. Emmons, Travis E. Stevens
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Patent number: 4137304Abstract: Cyclic and acyclic amides, substituted ureas and sulphonamides are disclosed having the property of stimulating the cold receptors of the nervous system of the body to produce a cold sensation and are used for this purpose in a variety of edible and topical preparations.Type: GrantFiled: June 2, 1977Date of Patent: January 30, 1979Assignee: Wilkinson Sword LimitedInventors: David G. Rowsell, Roger Hems
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Patent number: 4133880Abstract: N.sup.2 -substituted-L-arginine esters and amides, and the pharmaceutically acceptable acid addition salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis.Type: GrantFiled: July 28, 1977Date of Patent: January 9, 1979Assignees: Mitsubishi Chemical Industries Ltd., Shosuke OkamotoInventors: Shosuke Okamoto, Akiko Hijikata, Ryoji Kikumoto, Yoshikuni Tamao, Kazuo Ohkubo, Tohru Tezuka, Shinji Tonomura
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Patent number: 4118501Abstract: 4-(Sulfamoyl-phenyl)-4-hydroxy-2-imino-thiazolidine-derivatives having salidiuretic activity and a process for their manufacture.Type: GrantFiled: January 14, 1977Date of Patent: October 3, 1978Assignee: Hoechst AktiengesellschaftInventors: Hans-Jochen Lang, Roman Muschaweck
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Patent number: 4096321Abstract: A novel synthetic process to produce the antibiotic oxazinomycin is presented along with novel intermediates utilized in said process.Type: GrantFiled: November 22, 1976Date of Patent: June 20, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Manfred Weigele, Silvano DeBernardo
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Patent number: 4081449Abstract: Heterocyclic esters of alkylphenyl benzopyranopyridines represented by the formula ##STR1## wherein R.sub.1 is hydrogen, loweralkyl, loweralkanoyl, cycloalkylloweralkyl, cycloalkylloweralkanoyl, loweralkenyl, loweralkynyl, haloloweralkenyl, phenylloweralkyl, phenylloweralkenyl or phenylloweralkynyl; R.sub.2 is loweralkyl; R.sub.3 is ##STR2## WHEREIN X is a straight or branched chain alkylene group having from one to eight carbon atoms, a is an integer from 1 to 4, b is an integer from 1 to 4 and Z is CH.sub.2, O, S or NR.sub.7, with R.sub.7 being hydrogen or loweralkyl, with the limitation that when X is O, S or NR.sub.7, the sum of a and b is 3 or 4; and R.sub.8 is hydrogen or loweralkyl; Y is a straight or branched chain alkylene group having from one to ten carbon atoms; and each R.sub.4 and R.sub.5 and R.sub.6 are the same or different members of the group consisting of hydrogen, halo, trifluoromethyl or loweralkyl; and the pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: April 5, 1973Date of Patent: March 28, 1978Assignee: Abbott LaboratoriesInventor: Martin Winn
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Patent number: 4044010Abstract: Compounds of the formfulas ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, m and n and X are as hereinafter set forth,Are described. The compounds of formulas I and Ia are useful as neuroleptic agents.Type: GrantFiled: February 4, 1976Date of Patent: August 23, 1977Assignee: Hoffmann-La Roche Inc.Inventors: Max Gerecke, Jean-Pierre Kaplan, Emilio Kyburz