Patents by Inventor Heribert Offermanns
Heribert Offermanns has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 4055653Abstract: Compounds are prepared of the formula: ##STR1## wherein A is a straight or branched chain alkylene or alkylidene radical having 2 to 5 carbon atoms and which is substituted by an alkylthio group having 1 to 4 carbon atoms, a carboxymethyl thio group, a carboxyethyl thio group, an alkylsulfonyl group having 1 to 4 carbon atoms, a mercapto group, or the substituent on A together with --COR.sub.4 forms a 4 to 7 membered thiolactone ring, or A is substituted by an acylmercapto group wherein the acyl is benzoyl, a benzoyl radical substituted with one, two or three alkoxy groups with 1 to 6 carbon atoms, an alkanoyl radical of 1 to 6 carbon atoms, an alkenoyl radical of 3 to 6 carbon atoms, R.sub.1, R.sub.2 and R.sub.3 are the same or different and are alkyl groups of 1 to 5 carbon atoms and one of R.sub.1, R.sub.2 and R.sub.3 also can be hydrogen or the acyl radical of an alkanoic acid of 2 to 4 carbon atoms and R.sub.Type: GrantFiled: May 18, 1976Date of Patent: October 25, 1977Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Heribert Offermanns, Klaus Posselt
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Patent number: 4045479Abstract: Penicillamine or a homolog thereof is made by reacting an aldehyde branched at the .alpha.-carbon atom, sulfur and ammonia to form a thiazoline- .DELTA..sup.3 ; converting the latter compound by reaction with anhydrous hydrogen cyanide into the corresponding thiazolidine-4-carbonitrile; hydrolyzing the nitrile with an aqueous concentrated hydrochloric acid containing at least 30% by weight of hydrogen chloride at a temperature between 40.degree. and 70.degree. C to form the hydrochloric salt of the thiazolidine-4-acid amide and then, at a higher temperature continuing the hydrolysis to form the salt of the thiazolidine-4-carboxylic acid together with the ammonium salt. The ammonium salt is then separated from the mixture and the carboxylic acid hydrochloride is hydrolytically decomposed whereby the penicillamine is obtained.Type: GrantFiled: July 25, 1975Date of Patent: August 30, 1977Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Friedrich Asinger, Heribert Offermanns, Karl-Heinz Gulzek
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Patent number: 4028406Abstract: Improvements in the process of preparing penicillamine or a homolog thereof by reacting an .alpha.-carbon atom branched aldehyde, sulfur and ammonia to form a thiazoline-.DELTA..sup.3, reacting the thiazoline-.DELTA..sup.3 with anhydrous hydrogen cyanide to form a thiazolidine-4-carbonitrile, hydrolyzing the nitrile to form a mixture of the salt of the thiazolidine-4-carboxylic acid and ammonium salts, separating off the ammonium salts and hydrolytically decomposing the thiazolidine-4-carboxylic acid, wherein under the action of a mineral acid the thiazolidine-4-carbonitrile is in the first stage converted at low temperatures into the salt of the thiazolidine-4-carbonamide and then at higher temperatures converted into the salt of the thiazolidine-4-carboxylic acid.Type: GrantFiled: February 13, 1976Date of Patent: June 7, 1977Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Friedrich Asinger, Heribert Offermanns, Karl-Heinz Gluzek
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Patent number: 4012397Abstract: There are prepared compounds of the formula ##STR1## where R.sub.1 is halogen, R.sub.2 and R.sub.3 are hydrogen, halogen, trifluoromethyl, hydroxy, cyano, lower alkyl or lower alkoxy, R.sub.4 is hydrogen or lower alkyl, and R.sub.5 is hydrogen, lower alkyl, benzoyl, substituted benzoyl, lower carbalkoxy or ##STR2## where A is oxygen, sulfur, imino or lower alkylimino and R.sub.6 is lower alkyl, lower alkyl having 1 to 3 halogen atoms, lower alkenyl, hydroxymethyl, carboxymethyl, carb-lower alkoxy methyl, amino lower alkyl or alkylaminoalkyl having 2 to 13 carbon atoms or where any hydroxy or primary or secondary amino group is substituted by an alkanoyl group of 2 to 8 carbon atoms, carbalkoxy having 1 to 6 carbon atoms, carbophenoxy or carbobenzyloxy or a pharmacologically acceptable salt thereof. The compounds are useful in emotional disturbances, tension, anxiety, increased irritability.Type: GrantFiled: February 26, 1976Date of Patent: March 15, 1977Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Walter von Bebenburg, Heribert Offermanns
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Patent number: 4009271Abstract: There are produced 6-aza-3H-1,4-benzodiazepines and 6-aza-1,2-dihydro-3H-1,4-benzodiazepines of the formula: ##STR1## wherein R.sub.1 is the group --NR.sub.a R.sub.b or --NR.sub.a R.sub.b R.sub.c halide and R.sub.a and R.sub.b are the same or different and are hydrogen, alkyl groups of 1 to 6 carbon atoms, or alkyl groups of 1 to 6 carbon atoms substituted by hydroxy, phenyl or a carboxy group, and R.sub.c can be as defined for R.sub.a and R.sub.b except it cannot be hydrogen and wherein the group --NR.sub.a R.sub.b also can be a saturated closed 5, 6 or 7 membered ring which in a given case has a further oxygen atom or nitrogen atom or contains a nitrogen atom substituted with an alkyl group having 1 to 4 carbon atoms;R.sub.2 and R.sub.3 are the same or different and are hydrogen, halogen, trifluoromethyl, nitro, nitrile, hydroxy, lower alkyl or lower alkoxy;R.sub.4 is hydrogen;Z is a nitrogen atom or the NO group;R.sub.Type: GrantFiled: June 25, 1975Date of Patent: February 22, 1977Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Walter VONBebenburg, Heribert Offermanns
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Patent number: 4008223Abstract: There are produced 6-aza-3H-1, 4-benzodiazepines and 6-aza-1,2-dihydro-3H-1,4-benzodiazepines of the formula ##STR1## where R.sub.1 is a halogen, R.sub.2 and R.sub.3 are hydrogen, halogen, trifluoromethyl, nitro, nitrile, hydroxy, lower alkyl, lower alkoxy, R.sub.4 is hydrogen, hydroxyl, hydroxyl acylated with a mono or dicarboxylic aid of 2 to 6 carbon atoms, lower alkoxy, lower alkyl, benzyl, lower aliphatic acyl, carboxy or carb-lower alkoxy, Z is nitrogen or NO, R.sub.5 is hydrogen, lower alkyl, lower alkyl substituted with cycloalkyl of 3 to 6 carbon atoms, lower alkenyl, cycloalkyl of 3 to 6 carbon atoms , lower hydroxyalkyl, benzyl, aliphatic acyl of 2 to 6 carbon atoms aminoalkyl of 2 to 7 carbon atoms, mono or di lower alkyl substituted aminoalkyl of 2 to 7 carbon atoms, lower alkyl substituted with 5 to 7 membered N-heterocyclic ring, containing 0 to 1 additional nitrogen or oxygen atoms, and A is oxygen, sulfur, =NR.sub.5, =NOR.sub.5, =NH-NHR.sub.5 or two hydrogen atoms and the --N(R.sub.Type: GrantFiled: September 19, 1974Date of Patent: February 15, 1977Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Walter Von Bebenburg, Heribert Offermanns
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Patent number: 3981910Abstract: Compounds are prepared of the formula: ##SPC1##Wherein A is a straight or branched chain alkylene or alkylidene radical having 2 to 5 carbon atoms and which is substituted by an alkylthio group having 1 to 4 carbon atoms, a carboxymethyl thio group, a carboxyethyl thio group, an alkylsulfonyl group having 1 to 4 carbon atoms, a mercapto group, or the substituent on A together with --COR.sub.4 forms a 4 to 7 membered thiolactone ring, or A is substituted by an acylmercapto group wherein the acyl is benzoyl, a benzoyl radical substituted with one, two or three alkoxy groups with 1 to 6 carbon atoms, an alkanoyl radical of 1 to 6 carbon atoms, an alkenoyl radical of 3 to 6 carbon atoms, R.sub.1, R.sub.2 and R.sub.3 are the same or different and are alkyl groups of 1 to 5 carbon atoms and one of R.sub.1, R.sub.2 and R.sub.3 also can be hydrogen or the acyl radical of an alkanoic acid of 2 to 4 carbon atoms and R.sub.Type: GrantFiled: May 8, 1974Date of Patent: September 21, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Heribert Offermanns, Klaus Posselt
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Patent number: 3980665Abstract: D,L-penicillamine is converted to D-penicillamine with the aid of L-lysine.Type: GrantFiled: January 25, 1974Date of Patent: September 14, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Rudolf Fahnenstich, Joachim Heese, Heribert Offermanns
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Patent number: 3972873Abstract: There are prepared compounds of the formula: ##SPC1##Wherein:n is an integer from 1 to 4;R.sub.1 is alkyl of 1 to 6 carbon atoms, a hydroxy group, an amino group, an alkoxy group having 1 to 6 carbon atoms, a phenyl group or a phenyl group substituted with alkyl of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, trifluoromethyl, fluorine or chlorine;A is oxygen, sulfur, the imino group, or an alkylimino group having 1 to 6 carbon atoms, or when R.sub.1 is phenyl or substituted phenyl A also is two alkoxy groups having 1 to 6 carbon atoms or alkylenedioxy with 2 to 4 carbon atoms or --C(R.sub.1)=A is the cyano group;B is oxygen, sulfur, an imino group or an alkylimino group having 1 to 6 carbon atoms;R.sub.2 is hydrogen, a hydroxy group, an alkyl group with 1 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, or the group --O(CH.sub.2).sub.n -- C(=A)--R.sub.1 ;N.sub.o is nitrogen or an N-oxide group; andR.sub.3 and R.sub.Type: GrantFiled: May 9, 1975Date of Patent: August 3, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Walter von Bebenburg, Heribert Offermanns
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Patent number: 3969361Abstract: There are prepared compounds of the formula ##SPC1##Where R.sub.1 is halogen, R.sub.2 and R.sub.3 are hydrogen, halogen, trifluoromethyl, hydroxy, cyano, lower alkyl or lower alkoxy, R.sub.4 is hydrogen or lower alkyl, and R.sub.5 is hydrogen, lower alkyl, benzoyl, substituted benzoyl, lower carbalkoxy or ##EQU1## where A is oxygen, sulfur, imino or lower alkylimino and R.sub.6 is lower alkyl, lower alkyl having 1 to 3 halogen atoms, lower alkenyl, hydroxymethyl, carboxymethyl, carb-lower alkoxy methyl, amino lower alkyl or alkylaminoalkyl having 2 to 13 carbon atoms or where any hydroxy or primary or secondary amino group is substituted by an alkanoyl group of 2 to 8 carbon atoms, carbalkoxy having 1 to 6 carbon atoms, carbophenoxy or carbobenzyloxy or a pharmacologically acceptable salt thereof. The compounds are useful in emotional disturbances, tension, anxiety, increased irritability.Type: GrantFiled: August 15, 1974Date of Patent: July 13, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Walter VON Bebenburg, Heribert Offermanns
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Patent number: 3966752Abstract: The D-form of an optically active protected penicillamine is prepared by treating a solution of D,L protected penicillamine of the formula: ##EQU1## wherein Ac is formyl, and R.sub.1 and R.sub.2 are both methyl or are joined together to form the pentamethylene group.Type: GrantFiled: November 4, 1974Date of Patent: June 29, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Friedrich Asinger, Heribert Offermanns, Karl-Heinz Gluzek, Walter VONBebenburg
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Patent number: 3959302Abstract: The d,1-phenylpropanolamine(norephedrine) racemate is split with optically active thiazolidine-4-carboxylic acids of the formula: ##EQU1## where R.sub.1 and R.sub.2 are both methyl or are joined together to form the pentamethylene group.Type: GrantFiled: October 10, 1974Date of Patent: May 25, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Friedrich Asinger, Heribert Offermanns
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Patent number: 3956344Abstract: 2-BENZOYLPYRIDINE AND ITS DERIVATIVES SUBSTITUTED IN THE PYRIDINE AND/OR BENZENE RING ARE PREPARED BY OXIDIZING WITH HYDROGEN PEROXIDE OR OTHER PEROXIDE A COMPOUND OF THE FORMULA: ##SPC1##Where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen or a group inert under the oxidizing conditions and Y is cyano, carboxy or carbalkoxy in the presence of cyanate ion.Type: GrantFiled: December 20, 1974Date of Patent: May 11, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Walter Von Bebenburg, Heribert Offermanns
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Patent number: 3948984Abstract: Penicillamine and its hydrochloride are made by reacting isobutyraldehyde with elemental sulfur or a sulfur-containing compound and with gaseous ammonia so as to form 2-isopropyl-5.5-dimethyl-thiazoline-.DELTA..sup.3, then reacting the latter compound with substantially anhydrous hydrogen cyanide so as to form the corresponding thiazolidine 4-carbonitrile, thereupon treating the latter compound with an excess of concentrated hydrochloric acid at an elevated temperature and separating the components of the mixture formed and recovering the penicillamine hydrochloride which may then be converted to the free D,L-penicillamine.Type: GrantFiled: March 29, 1973Date of Patent: April 6, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Friedrich Asinger, Heribert Offermanns, Miklos Ghyczy
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Patent number: 3947464Abstract: The d,l-phenylpropanolamine racemate is split with optically active thiazolidine-4-carboxylic acids of the formula: ##EQU1## where R.sub.1 R.sub.2 are hydrogen, alkyl of 1 to 8 carbon atoms, cycloalkyl, aryl or alkylene of at least 2 carbon atoms or R.sub.1 and R.sub.2 together form a ring of alkyl or alkylene with 4 to 12 carbon atoms and AC is acyl, especially benzoyl, tosyl, nitrophenylsulfenyl, acetyl or preferably formyl.Type: GrantFiled: November 27, 1973Date of Patent: March 30, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Friedrich Asinger, Heribert Offermanns
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Patent number: 3946069Abstract: Penicillamine or a homolog thereof is obtained by reacting a 2-disubstituted-5,5-alkyl-thiazolidine nitrile, alkyl having 1 to 6 carbon atoms, with a mineral acid in a two-stage proceeding wherein in the first stage relatively low temperatures and a relatively high concentration of the mineral acid are employed while in the second stage the concentration of the acid is relatively low and the temperatures are relatively high, the term "relatively" referring to the relationship of said two stages of the reaction with mineral acid.Type: GrantFiled: December 20, 1972Date of Patent: March 23, 1976Assignee: Deutsche Gold-und Silber-Scheideanstalt vormals RoesslerInventors: Friedrich Asinger, Wolf Dieter Pfeifer, Heribert Offermanns, Paul Scherberich, Gerd Schreyer
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Patent number: 3941775Abstract: There are produced 6-aza-3H-1,4-benzodiazepines and 6-aza-1,2-dihydro-3H-1,4-benzodiazepines of the formula: ##SPC1##Wherein R.sub.1 is the group --NR.sub.a R.sub.b, --NR.sub.a R.sub.b R.sub.c or --NR.sub.a acyl and R.sub.a, R.sub.b and R.sub.c are the same or different and are hydrogen, alkyl groups of 1 to 6 carbon atoms, or alkyl groups of 1 to 6 carbon atoms substituted by hydroxy, an alkoxy group of 1 to 6 carbon atoms, a carboxy group, a nitrile group, a carbamide group, a carbalkoxy group with 1 to 6 carbon atoms in the alkoxy, a phenyl group or a halogen and acyl is an aliphatic acyl group with 2 to 6 carbon atoms and wherein the group --NR.sub.a R.sub.b also can be a saturated closed 5, 6 or 7 membered ring which in a given case has a further oxygen atom or nitrogen atom or contains a nitrogen atom substituted with an alkyl group having 1 to 4 carbon atoms;R.sub.2 and R.sub.Type: GrantFiled: April 12, 1974Date of Patent: March 2, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Walter von Bebenburg, Heribert Offermanns
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Patent number: 3933813Abstract: Compounds having a mercaptoethyl group are prepared by reacting an aqueous thiocyanate solution with ethylene oxide in the presence of an inert water immiscible organic solvent to form ethylene sulfide and then reacting the organic phase with a polar organic compound, preferably a secondary amine.Type: GrantFiled: December 29, 1972Date of Patent: January 20, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Helmut Beschke, Heribert Offermanns, Wilhelm-Alfons Schuler
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Patent number: 3932533Abstract: .alpha.- Bisabolol of plant origin is purified by being treated with alkali hydroxide, alkali alcoholate, alkali carbonate, alkali bicarbonate, alkaline earth hydroxide, alkaline earth oxide or aluminium hydroxide. Preferably activated carbon is also used in the purification. Preferably the .alpha.-bisabolol is treated with pure nitrogen gas before the alkali treatment.Type: GrantFiled: April 8, 1974Date of Patent: January 13, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Otto Isaac, Heribert Offermanns
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Patent number: 3931208Abstract: 2 AND 5 SUBSTITUTED THIAZOLINE-(3) COMPOUNDS OF THE FORMULA: ##EQU1## in which R.sub.1, R.sub.2, and R.sub.3 and R.sub.4 are the same or different, R.sub.1 and R.sub.2 are straight or branched chain lower alkyl, alkenyl or aralkyl groups or together are a straight or branched chain alkylene or ethylenically unsaturated divalent aliphatic hydrocarbon group which joins with the adjacent carbon atom to form a ring and R.sub.3 and R.sub.4 are similarly defined except R.sub.3 can also be hydrogen by reaching a 2,2' dioxodisulfide of the formula ##EQU2## with an oxo compound of the formula ##EQU3## and with ammonia and hydrogen sulfide in the presence of an amine and an ammonium salt.Type: GrantFiled: November 5, 1973Date of Patent: January 6, 1976Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Heribert Offermanns, Friedrich Asinger, Wolf-Dieter Pfeifer, Paul Scherberich, Gerd Schreyer