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).

  • Patent number: 4055653
    Abstract: 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: Grant
    Filed: May 18, 1976
    Date of Patent: October 25, 1977
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Heribert Offermanns, Klaus Posselt
  • Patent number: 4045479
    Abstract: 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: Grant
    Filed: July 25, 1975
    Date of Patent: August 30, 1977
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Friedrich Asinger, Heribert Offermanns, Karl-Heinz Gulzek
  • Patent number: 4028406
    Abstract: 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: Grant
    Filed: February 13, 1976
    Date of Patent: June 7, 1977
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Friedrich Asinger, Heribert Offermanns, Karl-Heinz Gluzek
  • Patent number: 4012397
    Abstract: 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: Grant
    Filed: February 26, 1976
    Date of Patent: March 15, 1977
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Walter von Bebenburg, Heribert Offermanns
  • Patent number: 4009271
    Abstract: 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: Grant
    Filed: June 25, 1975
    Date of Patent: February 22, 1977
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Walter VONBebenburg, Heribert Offermanns
  • Patent number: 4008223
    Abstract: 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: Grant
    Filed: September 19, 1974
    Date of Patent: February 15, 1977
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Walter Von Bebenburg, Heribert Offermanns
  • Patent number: 3981910
    Abstract: 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: Grant
    Filed: May 8, 1974
    Date of Patent: September 21, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Heribert Offermanns, Klaus Posselt
  • Patent number: 3980665
    Abstract: D,L-penicillamine is converted to D-penicillamine with the aid of L-lysine.
    Type: Grant
    Filed: January 25, 1974
    Date of Patent: September 14, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Rudolf Fahnenstich, Joachim Heese, Heribert Offermanns
  • Patent number: 3972873
    Abstract: 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: Grant
    Filed: May 9, 1975
    Date of Patent: August 3, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Walter von Bebenburg, Heribert Offermanns
  • Patent number: 3969361
    Abstract: 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: Grant
    Filed: August 15, 1974
    Date of Patent: July 13, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Walter VON Bebenburg, Heribert Offermanns
  • Patent number: 3966752
    Abstract: 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: Grant
    Filed: November 4, 1974
    Date of Patent: June 29, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Friedrich Asinger, Heribert Offermanns, Karl-Heinz Gluzek, Walter VONBebenburg
  • Patent number: 3959302
    Abstract: 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: Grant
    Filed: October 10, 1974
    Date of Patent: May 25, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Friedrich Asinger, Heribert Offermanns
  • Patent number: 3956344
    Abstract: 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: Grant
    Filed: December 20, 1974
    Date of Patent: May 11, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Walter Von Bebenburg, Heribert Offermanns
  • Patent number: 3948984
    Abstract: 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: Grant
    Filed: March 29, 1973
    Date of Patent: April 6, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Friedrich Asinger, Heribert Offermanns, Miklos Ghyczy
  • Patent number: 3947464
    Abstract: 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: Grant
    Filed: November 27, 1973
    Date of Patent: March 30, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Friedrich Asinger, Heribert Offermanns
  • Patent number: 3946069
    Abstract: 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: Grant
    Filed: December 20, 1972
    Date of Patent: March 23, 1976
    Assignee: Deutsche Gold-und Silber-Scheideanstalt vormals Roessler
    Inventors: Friedrich Asinger, Wolf Dieter Pfeifer, Heribert Offermanns, Paul Scherberich, Gerd Schreyer
  • Patent number: 3941775
    Abstract: 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: Grant
    Filed: April 12, 1974
    Date of Patent: March 2, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Walter von Bebenburg, Heribert Offermanns
  • Patent number: 3933813
    Abstract: 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: Grant
    Filed: December 29, 1972
    Date of Patent: January 20, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Helmut Beschke, Heribert Offermanns, Wilhelm-Alfons Schuler
  • Patent number: 3932533
    Abstract: .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: Grant
    Filed: April 8, 1974
    Date of Patent: January 13, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Otto Isaac, Heribert Offermanns
  • Patent number: 3931208
    Abstract: 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: Grant
    Filed: November 5, 1973
    Date of Patent: January 6, 1976
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Heribert Offermanns, Friedrich Asinger, Wolf-Dieter Pfeifer, Paul Scherberich, Gerd Schreyer