Patents by Inventor Goetz E. Hardtmann

Goetz E. Hardtmann 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: 4870199
    Abstract: Process for the synthesis of compounds of the formula ##STR1## in R[R*,S*] enantiomeric form, wherein each P.sub.1 is independently an hydroxy group-protecting group, andR.sub.2z is C.sub.1-4 alkyl, benzyl or allyl,comprising, as a key step when R.sub.2z is R.sub.2x, the reaction of the compound of the formula ##STR2## in (S) enantiomeric form with a compound of the formulaMg.sup. .circle.+2 (.sup..crclbar. OOC--CH.sub.2 --COOR.sub.2x).sub.2to obtain a compound of the formula ##STR3## in (S) enantiomeric form, and, as a key step when R.sub.2z is R.sub.2y, the reaction of a compound of the formula ##STR4## in (S) enantioimeric form with a compound of the formulaLi.sup..sym..crclbar. CH.sub.2 --COOR.sub.2yto obtain a compound of the formula ##STR5## in (S) enantiomeric form, wherein R.sub.2x is primary or secondary C.sub.1-4 alkyl, benzyl or allyl,R.sub.2y is C.sub.1-4 alkyl not containing an asymmetric carbon atom, andR.sub.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: September 26, 1989
    Assignee: Sandoz Pharm. Corp.
    Inventors: Kau-Ming Chen, Goetz E. Hardtmann, Prasad K. Kapa, George T. Lee, Jerome Linder, Sompong Wattanasin
  • Patent number: 4760065
    Abstract: Trifluoromethyl substituted tetracyclic compounds including optical isomers thereof having the formula: ##STR1## wherein n is 1 or 2 and p is 0 or 1, are useful as CNS agents with tranquilizing effects.
    Type: Grant
    Filed: February 13, 1986
    Date of Patent: July 26, 1988
    Inventors: Goetz E. Hardtmann, William J. Houlihan, Rudolf K. A. Giger
  • Patent number: 4452787
    Abstract: Tranquilizers are of the formula I: ##STR1## wherein R.degree. is hydrogen, halo of atomic weight of from 18 to 80, i.e. fluoro, chloro or bromo, or alkyl of 1 to 3 carbon atoms,R is hydrogen, halo of atomic weight of from 18 to 80, alkyl of 1 to 4 carbon atoms, nitro or trifluoromethyl,n is 0 or 1,R.sub.1, R.sub.2 and R.sub.3 are each independently hydrogen or alkyl of 1 or 2 carbon atoms, with the proviso that no more than 2 of R.sub.1, R.sub.2 and R.sub.3 are other than hydrogen,Z is ##STR2## R' is hydrogen or alkyl of 1 or 2 carbon atoms, Y.degree. is hydrogen, halo of atomic weight of from 18 to 80 or alkyl of 1 to 3 carbon atoms,Y is hydrogen, halo of atomic weight of from 18 to 80, alkyl of 1 to 4 carbon atoms, trifluoromethyl or nitro,p is 1 or 2,q is 0, 1 or 2, andm is 0, 1, 2, 3 or 4.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: June 5, 1984
    Assignee: Sandoz, Inc.
    Inventors: Goetz E. Hardtmann, William J. Houlihan
  • Patent number: 4451464
    Abstract: Tranquilizers are of the formula: ##STR1## wherein R.degree. is alkyl of 1 to 8 carbon atoms, andn is 1 or 2.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: May 29, 1984
    Assignee: Sandoz, Inc.
    Inventors: Goetz E. Hardtmann, William J. Houlihan
  • Patent number: 4451448
    Abstract: Minor tranquilizers preparable by known processes are represented by the following structural formula I: ##STR1## wherein R.sup.o is hydrogen, halo of atomic weight of from 18 to 80, i.e. fluoro, chloro or bromo or alkyl of 1 to 3 carbon atoms,R is halo of atomic weight of from 18 to 80, alkyl of 1 to 4 carbon atoms or trifluoromethyl,R' is alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, norbornyl, alkyl of 1 to 3 carbon atoms substituted by cycloalkyl of 3 to 7 carbon atoms or --CH.sub.2 (F.sub.x ALK) wherein x is 1 to 3 and ALK is alkyl of 1 to 4 carbon atoms,R.sub.1, R.sub.2, and R.sub.3 are independently hydrogen or alkyl of 1 or 2 carbon atoms, andn is 0 or 1.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: May 29, 1984
    Assignee: Sandoz, Inc.
    Inventors: Goetz E. Hardtmann, William J. Houlihan
  • Patent number: 4412952
    Abstract: Conversion of 3-acyloxy-benzodiazepin-2-ones into corresponding 3-hydroxy benzodiazepin-2-ones is carried out efficiently with potassium hydroxide or potassium alkoxide as catalyst in lower alkanol solvent at a pH of 11-11.5. The final products, which include temazepam, are useful as sleep inducers.
    Type: Grant
    Filed: April 30, 1982
    Date of Patent: November 1, 1983
    Assignee: Sandoz, Inc.
    Inventors: Goetz E. Hardtmann, Oljan Repic, Susi Vogt
  • Patent number: 4281131
    Abstract: Disclosed are compounds which are 4-hydroxy-2-quinolinone-3-carboxylic acids and salts thereof, e.g., 1-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid, useful as anti-allergic agents, and prepared by hydrolysis of the corresponding carboxylic acid esters.
    Type: Grant
    Filed: July 16, 1979
    Date of Patent: July 28, 1981
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4273930
    Abstract: Disclosed are compounds which are 4-hydroxy-2-quinolinone-3-carboxylic acid esters, e.g., 1-methyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester, useful as anti-allergic agents and intermediates for 1-alkyl-4-alkoxy-quinolin-2(1H)-ones, and prepared by reacting an isatoic anhydride with an alkali metal salt of a malonic ester.
    Type: Grant
    Filed: August 9, 1979
    Date of Patent: June 16, 1981
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4264602
    Abstract: Anti-allergic 4-hydroxy-3-nitro-pyrido[2,3-b]pyridines-2(1H)-ones are prepared by reacting a 3,4-dihydro-1,3-dioxo-1H-pyrido[2,3-d][1,3]oxazine (a 3-azaisatoic anhydride) with the carbanion resulting from the reaction of nitro acetic acid alkyl esters with a proton abstracting agent.
    Type: Grant
    Filed: July 21, 1976
    Date of Patent: April 28, 1981
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4221797
    Abstract: The compounds are amino- or cyano-bearing dihydroquinolines, which have either of the combinations of (a) 2-amino, 3-carboxylic and 4-oxo functions, or (b) 2-oxo, 3-cyano and 4-hydroxy functions, and may be optionally substituted at 1 or 2 of the 5, 6, 7 or 8 positions, eg 1-allyl-2-amino-1,4-dihydro-6,7-dimethoxy-4-oxo-quinoline-3-carboxylic acid ethyl ester, and 1-allyl 3-cyano-1,2-dihydro-4-hydroxy-6,7-dimethoxy-2-oxo-quinoline. The compounds are useful as pharmaceuticals.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: September 9, 1980
    Assignee: Sandoz, Inc.
    Inventors: Goetz E. Hardtmann, Gary M. Coppola
  • Patent number: 4192876
    Abstract: Anti-allergic 4-hydroxy-3-nitro-quinoline-2(1H)-ones are prepared by reacting an isatoic anhydride with the carbanion resulting from the treatment of nitro acetic acid alkyl esters with a proton abstracting agent.
    Type: Grant
    Filed: June 20, 1977
    Date of Patent: March 11, 1980
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4190659
    Abstract: Disclosed are compounds which are 4-hydroxy-2-quinolinone-3-carboxylic acid esters, e.g., 1-methyl-4-hydroxy-2-quinolinone-3-carboxylic acid ethyl ester, useful as anti-allergic agents and intermediates for 1-alkyl-4-alkoxy-quinolin-2(1H)-ones, and prepared by reacting an isatoic anhydride with an alkali metal salt of a malonic ester.
    Type: Grant
    Filed: June 20, 1977
    Date of Patent: February 26, 1980
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4187309
    Abstract: Disclosed are compounds which are 4-hydroxy-2-quinolinone-3-carboxylic acids and salts thereof, e.g., 1-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid, useful as anti-allergic agents, and prepared by hydrolysis of the corresponding carboxylic acid esters.
    Type: Grant
    Filed: June 20, 1977
    Date of Patent: February 5, 1980
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4169893
    Abstract: Anti-allergic 4-hydroxy-naphthpyridine-2(1H)-one-3-carboxylic acids and esters are prepared by reacting a 1,3-dioxo-1-naphth[4,5-b]oxazine with an alkali metal salt of a malonic ester (and hydrolyzing to obtain the acids).
    Type: Grant
    Filed: March 13, 1978
    Date of Patent: October 2, 1979
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4160032
    Abstract: Sleep inducers of the formula: ##STR1## wherein R is hydrogen or halo of atomic weight of from 18 to 36, R' is hydrogen, halo or CF.sub.3 and R.degree. is hydrogen or lower alkyl. Preparation by cyclizing a 2-nitro-phenylacetic acid is also disclosed.
    Type: Grant
    Filed: November 18, 1974
    Date of Patent: July 3, 1979
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4128649
    Abstract: Anti-allergic 4-hydroxy-pyrido[2,3-b]pyridine-2(1H)-one-3-carboxylic acids and esters are prepared by reacting a 3,4-dihydro-1,3-dioxo-1H-pyrido[2,3-d][1,3]oxazine (a 3-azaisatoic anhydride) with an alkali metal salt of a malonic ester.
    Type: Grant
    Filed: June 29, 1977
    Date of Patent: December 5, 1978
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4127574
    Abstract: Anti-allergic 4-hydroxy-3-sulfonyl-quinolin-2(1H)-ones are prepared by reacting an isatoic anhydride with the carbanion resulting from the treatment of sulfonyl acetic acid alkyl esters with a proton abstracting agent.
    Type: Grant
    Filed: March 1, 1976
    Date of Patent: November 28, 1978
    Assignee: Sandoz, Inc.
    Inventors: Goetz E. Hardtmann, Gary M. Coppola
  • Patent number: 4124587
    Abstract: Anti-allergic 4-hydroxy-3-sulfinyl-quinolin-2(1H)-ones are prepared by reacting an isatoic anhydride with the carbanion resulting from the treatment of sulfinyl acetic acid alkyl esters with a proton abstracting agent.
    Type: Grant
    Filed: March 1, 1976
    Date of Patent: November 7, 1978
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann
  • Patent number: 4124588
    Abstract: Anti-allergic 4-hydroxy-3-quinoline-2-one-3-phosphonic acid esters are prepared by reacting an isatoic anhydride with the carbanion resulting from the treatment of phosphono acetic acid alkyl esters with a proton abstracting agent.
    Type: Grant
    Filed: March 1, 1976
    Date of Patent: November 7, 1978
    Assignee: Sandoz, Inc.
    Inventors: Goetz E. Hardtmann, Gary M. Coppola
  • Patent number: 4119720
    Abstract: Disclosed are compounds which are unsaturated esters of 4-hydroxy-2-quinolinone-3-carboxylic acids, e.g., 1-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester, useful as anti-allergic agents, and prepared by reacting an isatoic anhydride with an alkali metal salt of a malonic acid unsaturated ester.
    Type: Grant
    Filed: July 6, 1977
    Date of Patent: October 10, 1978
    Assignee: Sandoz, Inc.
    Inventor: Goetz E. Hardtmann