Patents Represented by Attorney Robert E. Carnahan
  • Patent number: 4680389
    Abstract: Crystalline adducts of 7-[(Z)-2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido-3-[(1-methyl-1-pyrr olidinium)methyl]-3-cephem-4-carboxylate selected from the group consisting of the di(1-methyl-2-pyrrolidinone) adduct and the di(N-formyl pyrrolidine) adduct and salt complexes thereof have been found to be stable at even high temperatures. The crystalline adducts are prepared by forming an admixture of adducting agents, zwitterions and seed adduct crystals and inducing crystallization followed by isolating the crystals. A process for preparing adduct salt complexes is also disclosed. Crystalline zwitterion can be formed by slurrying the adducts in a solvent which removes the adducting agents.
    Type: Grant
    Filed: January 10, 1986
    Date of Patent: July 14, 1987
    Assignee: Bristol-Myers Company
    Inventors: Murray A. Kaplan, Joseph B. Bogardus, Robert A. Lipper
  • Patent number: 4675409
    Abstract: A new and novel process for the preparation of encainide (4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]-benzanilide) has been developed. The process utilizes .alpha.-picoline, O-nitrobenzaldehyde, and anisoyl chloride as starting materials.
    Type: Grant
    Filed: February 25, 1986
    Date of Patent: June 23, 1987
    Assignee: Bristol-Myers Company
    Inventors: John L. Dillon, Richard H. Spector
  • Patent number: 4668687
    Abstract: A series of nootropic compounds of the following formula: ##STR1## and its pharmaceutically acceptable acid addition salts, wherein: R.sup.2 is hydrogen, lower alkyl, aryl which is optimally substituted, or hetaryl;R.sup.7 is hydrogen or is combined with R.sup.9 as a fused benzo-ring;R.sup.8 is hydrogen or lower alkyl; andR.sup.9 is lower alkyl, or R.sup.9 can be combined with R.sup.8 to give a 2-pyrrolidinone, a phthalimide, or isoindolone ring system.Pharmacological testing demonstrates that the series possesses cognition and memory enhancing actions and/or mild CNS simulation.
    Type: Grant
    Filed: November 19, 1985
    Date of Patent: May 26, 1987
    Assignee: Bristol-Myers Company
    Inventors: Joseph P. Yevich, Ronald J. Mattson
  • Patent number: 4661590
    Abstract: 3-[(Z)-1-Propen-1-yl]-7-acylamido cephalosporins in which the 7-acyl group is phenylglycyl or substituted phenylglycyl are orally active antibiotics against Gram+ and Gram- bacteria.
    Type: Grant
    Filed: July 31, 1985
    Date of Patent: April 28, 1987
    Assignee: Bristol-Myers Company
    Inventors: Hideaki Hoshi, Jun Okumura, Takayuki Naito, Yoshio Abe, Shimpei Aburaki
  • Patent number: 4658058
    Abstract: The novel compound N-[(3-aminoproypl)aminobutyl]-Z-(F-guandino-3-hydroxyheptanamido)-2-methox yethanamide or a pharmaceutically acceptable salt thereof which has antitumor activity in experimental animals.
    Type: Grant
    Filed: April 15, 1985
    Date of Patent: April 14, 1987
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Hamao Umezawa, Tomio Takeuchi, Shinichi Kondo, Hironobu Iinuma, Daishiro Ikeda, Teruya Nakamura, Akio Fujii
  • Patent number: 4652644
    Abstract: There is disclosed a process for the preparation of N.sup.7 -amidino substituted mitomycin C derivatives. The process comprises reacting mitomycin C or an N.sup.1a substituted derivative thereof such as porfiromycin with a chloroformimidinium salt in a polar solvent at low temperature. This reaction is conducted in the presence of a tertiary amine. This process eliminates the need for a strong base such as NaH prior to addition of a chloroformimidinium salt.
    Type: Grant
    Filed: April 29, 1985
    Date of Patent: March 24, 1987
    Assignee: Bristol-Myers Company
    Inventors: Takushi Kaneko, Henry S. L. Wong
  • Patent number: 4642352
    Abstract: 7-Acylamino-9a-methoxymitosanes having enhanced capacity to inhibit animal tumors in vivo relative to mitomycin C are produced by N.sup.7 -acylation of 7-amino-9a-methoxymitosane, or N.sup.1a,N.sup.7 -diacylation thereof. Carboxamide, thiocarboxamide, urea, thiourea, urethane, thiophosphoramide, phosphoramide, and sulfonamide derivatives are disclosed.
    Type: Grant
    Filed: December 23, 1983
    Date of Patent: February 10, 1987
    Assignee: Bristol-Myers Company
    Inventors: Takushi Kaneko, Henry S. L. Wong, Terrence W. Doyle
  • Patent number: 4634703
    Abstract: Buspirone and its pharmaceutically acceptable salts are useful in alleviation of panic disorders which can take the form of clinical syndromes comprising, for example, panic attacks, agoraphobia and phobic anxiety.
    Type: Grant
    Filed: October 25, 1985
    Date of Patent: January 6, 1987
    Assignee: Bristol-Myers Company
    Inventors: Neil M. Kurtz, Roger E. Newton, Davis L. Temple, Jr.
  • Patent number: 4625020
    Abstract: Process for producing 1-halo-2-deoxy-2-fluoroarabinofuranoside derivatives bearing protective ester groups from 1,3,5-tri-O-acylribofuranose; the 1-halo compounds are intermediates in the synthesis of therapeutically active nucleosidic compounds.
    Type: Grant
    Filed: November 18, 1983
    Date of Patent: November 25, 1986
    Assignee: Bristol-Myers Company
    Inventors: Steven P. Brundidge, Henry G. Howell, Chester Sapino, Jr., Chon-Hong Tann
  • Patent number: 4619925
    Abstract: The present invention relates to 7-[(D)-2-amino-2-(3-hydroxyphenyl)acetamido]-3-[(Z)-1-propenyl]-3-cephem-4 -carboxylic acid, which is an orally active antibiotic against Gram-positive and Gram-negative bacteria.
    Type: Grant
    Filed: November 8, 1985
    Date of Patent: October 28, 1986
    Assignee: Bristol-Myers Company
    Inventors: Hideaki Hoshi, Takayuki Naito
  • Patent number: 4618680
    Abstract: 4-Hydroxy-3-methoxy-N-[2-[2-(1-methyl-2-piperidinyl)ethyl]-phenyl]benzamide is an antiarrhythmic agent having relatively low toxicity and increased duration of action.
    Type: Grant
    Filed: November 27, 1981
    Date of Patent: October 21, 1986
    Assignee: Mead Johnson & Company
    Inventors: Robert F. Mayol, Richard E. Gammans
  • Patent number: 4591641
    Abstract: 3-[(Z)-1-Propen-1-yl]-7-acylamido cephalosporins in which the 7-acyl group is phenylglycyl or substituted phenylglycyl are orally active antibiotics against Gram+ and Gram- bacteria.
    Type: Grant
    Filed: March 18, 1985
    Date of Patent: May 27, 1986
    Assignee: Bristol-Myers Company
    Inventors: Hideaki Hoshi, Jun Okumura, Takayuki Naito, Yoshio Abe, Shimpei Aburaki
  • Patent number: 4590074
    Abstract: Symmetrical bis-amidine derivatives of mitomycin C may be converted to unsymmetrical bis-amidine analogs by reaction with secondary amines. The compounds are active anti-tumor agents in experimental animal tumors.
    Type: Grant
    Filed: October 15, 1985
    Date of Patent: May 20, 1986
    Assignee: Bristol-Myers Company
    Inventors: Dolatrai M. Vyas, Takushi Kaneko, Terrence W. Doyle
  • Patent number: 4579737
    Abstract: Symmetrical bis-amidine derivatives of mitomycin C may be converted to unsymmetrical bis-amidine analogs by reaction with secondary amines. The compounds are active anti-tumor agents in experimental animal tumors.
    Type: Grant
    Filed: November 19, 1984
    Date of Patent: April 1, 1986
    Assignee: Bristol-Myers Company
    Inventors: Dolatrai M. Vyas, Takushi Kaneko, Terrence W. Doyle
  • Patent number: 4568490
    Abstract: An aminopropylaminobleomycin represented by the following formula or a salt thereof, which is minimized in side effects such as pulmonary toxicity:[BX]--NH--(CH.sub.2).sub.3 --A--)CH.sub.2).sub.3 --Bwherein[BX] represents the acyl group of bleomycinic acid whose formula differs from that of bleomycin acid by the removal of the hydroxyl group from the carboxyl group of said acid;A represents a group of the general formula ##STR1## wherein R.sub.1 is a lower alkyl or benzyl,R.sub.2 is a lower alkyl or benzyl,R is a lower alkylene, andn is 0 or 1; andB represents a group of the formula ##STR2## wherein (i) R.sub.3 is hydrogen and R.sub.4 is(a) benzyl substituted by one or more halogen atoms, provided that the benzyl is substituted by two halogen atoms when R.sub.
    Type: Grant
    Filed: June 12, 1985
    Date of Patent: February 4, 1986
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Hamao Umezawa, Akio Fujii, Yasuhiko Muraoka, Tokuji Nakatani, Takeyo Fukuoka, Katsutoshi Takahashi
  • Patent number: 4567256
    Abstract: 9a-Methoxymitosane derivatives having the amidino group at one or both of the 7-position and the carbamoyl-N positions are prepared by reaction of mitomycin A, mitomycin C, or an N.sup.1a -substituted analog thereof with an amide acetal, iminothioether, halomethyleniminium halide, or iminohalide salt.
    Type: Grant
    Filed: October 5, 1984
    Date of Patent: January 28, 1986
    Assignee: Bristol-Myers Company
    Inventors: Dolatrai M. Vyas, Takushi Kaneko, Terrence W. Doyle
  • Patent number: 4537880
    Abstract: An aminopropylaminobleomycin represented by the following formula or a salt thereof, which is minimized in side effects such as pulmonary toxicity:[BX]--NH--(CH.sub.2).sub.3 --A--(CH.sub.2).sub.3 --Bwherein[BX] represents the acyl group of bleomycinic acid whose formula differs from that of bleomycin acid by the removal of the hydroxyl group from the carboxyl group of said acid;A represents a group of the general formula ##STR1## wherein R.sub.1 is a lower alkyl or benzyl,R.sub.2 is a lower alkyl or benzyl,R is a lower alkylene, andn is 0 or 1; andB represents a group of the formula ##STR2## wherein (i) R.sub.3 is hydrogen and R.sub.4 is(a) benzyl substituted by one or more halogen atoms, provided that the benzyl is substituted by two halogen atoms when R.sub.
    Type: Grant
    Filed: July 27, 1984
    Date of Patent: August 27, 1985
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Hamao Umezawa, Akio Fujii, Yasuhiko Muraoka, Tokuji Nakatani, Takeyo Fukuoka, Katsutoshi Takahashi
  • Patent number: 4520022
    Abstract: 3-[(Z)-1-Propen-1-yl]-7-acylamido cephalosporins in which the 7-acyl group is phenylglycyl or substituted phenylglycyl are orally active antibiotics against Gram+ and Gram- bacteria.
    Type: Grant
    Filed: December 28, 1983
    Date of Patent: May 28, 1985
    Assignee: Bristol-Myers Company
    Inventors: Hideaki Hoshi, Jun Okumura, Takayuki Naito, Yoshio Abe, Shimpei Aburaki
  • Patent number: 4518802
    Abstract: N-[4-[(3-aminopropyl)amino]butyl]-2,2-dihydroxyethanamide is an immunostimulant in animals and an intermediate for synthesis of the antibiotic BMG162-aF2.
    Type: Grant
    Filed: February 27, 1984
    Date of Patent: May 21, 1985
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Hamao Umezawa, Tomio Takeuchi, Shinichi Kondo, Hironobu Iinuma, Daishiro Ikeda, Teruya Nakamura, Akio Fujii
  • Patent number: 4518532
    Abstract: N-[4-(3-Aminopropyl)aminobutyl]-2-(.omega.-guanidino-fatty acid-amido)-2-substituted-ethanamides represented by the general formula ##STR1## wherein Y represents --(CH.sub.2 --CH.sub.2 --, --CH.dbd.CH or ##STR2## R represents a hydrogen atom, an alkyl group of 1 to 4 carbon atoms which may have a hydroxyl group as substituent, or a benzyl group, and n is an integer of from 1 to 8, provided that when Y is ##STR3## and n is 4, R represents the groups other than the hydrogen atom; a salt thereof having antitumor activity in experimental animal tumors and a process for the preparation thereof is provided.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: May 21, 1985
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Hamao Umezawa, Tomio Takeuchi, Shinichi Kondo, Hironobu Iinuma, Daishiro Ikeda, Teruya Nakamura, Akio Fujii