Patents Represented by Attorney John J. Killinger
  • Patent number: 4097672
    Abstract: The present invention discloses amides and thioamides substituted in the .alpha. or .beta. position with substituted pyrazoles which are useful as herbicides.
    Type: Grant
    Filed: May 9, 1977
    Date of Patent: June 27, 1978
    Assignee: The Upjohn Company
    Inventors: Malcolm W. Moon, Gabriel Kornis
  • Patent number: 4089672
    Abstract: Certain new 1-(substituted-hydrocarbyl)-di- and trihalopyrazoles have been synthesized. They possess herbicidal and plant growth regulatory activity. The hydrocarbyl group, i.e., alkylene or alkenylene group at the 1-nitrogen of the pyrazole nucleus has either a carboxyl group, an hydroxymethyl group, an hydroxymethyl lower-alkanoate group a carboxylic lower-alkyl ester group a cyano group or a carboxylic amide group. The new compounds are prepared and isolated by conventional chemical reactions and procedures. An improved reaction for making the new carboxylic acids is described. Weed control methods and compositions for herbicidal use are also described.
    Type: Grant
    Filed: January 23, 1976
    Date of Patent: May 16, 1978
    Assignee: The Upjohn Company
    Inventors: Gabriel Kornis, Eldon G. Nidy, Henry J. Vostral, Arnolds Steinhards, deceased
  • Patent number: 4086254
    Abstract: This invention relates to novel compounds of the formula: ##STR1## wherein X is H, methoxy, bromine or chloro; R.sub.1 is hydrogen or hydroxy, acyloxy wherein acyl is 2 to 8 carbon atoms, R.sub.2 is hydrogen, hydroxy, methyl, fluoro or chloro; and R.sub.1 and R.sub.2 taken together can be ##STR2## R.sub.3 is hydrogen, methyl, chloro, or fluoro; R.sub.4 is hydrogen, chloro or fluoro; R.sub.5 is oxygen, .beta.-hydroxy or .beta.-chloro, with the proviso that when R.sub.5 is .beta.-chloro then R.sub.4 must be chloro.The compounds have a photocleavable group (R) which is removable by irradiation. The compounds have reduced activity in the uncleaved state and provide a therapeutically active compound upon irradiation at the site of irradiation.
    Type: Grant
    Filed: April 13, 1977
    Date of Patent: April 25, 1978
    Assignee: The Upjohn Company
    Inventor: Wendell Wierenga
  • Patent number: 4072498
    Abstract: The present invention discloses amides and thioamides substituted in the .alpha. or .beta. position with substituted pyrazoles which are useful as herbicides.
    Type: Grant
    Filed: May 14, 1976
    Date of Patent: February 7, 1978
    Assignee: The Upjohn Company
    Inventors: Malcolm W. Moon, Gabriel Kornis
  • Patent number: 4065556
    Abstract: A process for preparing tubercidin in a more acceptable form for injection consisting of mixing whole blood with a saline solution of tubercidin.
    Type: Grant
    Filed: May 24, 1976
    Date of Patent: December 27, 1977
    Assignee: The Upjohn Company
    Inventor: Charles G. Smith
  • Patent number: 4065573
    Abstract: A class of new 4-amino-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory, and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts.Processes for synthesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed.
    Type: Grant
    Filed: June 3, 1976
    Date of Patent: December 27, 1977
    Assignee: The Upjohn Company
    Inventor: Daniel Lednicer
  • Patent number: 4065574
    Abstract: Certain 4-chromones, 4-chromanones, 4-chromone oximes, and 4-chromanone oximes have been found to be active against fungi. These generally well-known compounds can be applied to seeds, plants, animals, objects, or places for preventing damage due to fungi. Specific, recognized active compounds, e.g., 6,8-dichloro-3-methyl-4-chromone oximes and 3-methyl-4-chromanone oximes are shown to be so useful in detail. General methods of preparing the active compounds are described.
    Type: Grant
    Filed: August 12, 1976
    Date of Patent: December 27, 1977
    Assignee: The Upjohn Company
    Inventors: Malcolm W. Moon, John C. Sharp
  • Patent number: 4064248
    Abstract: An improved dosage regimen for the administration of the pharmacologically acceptable salts or esters of a compound of the formula: ##STR1## wherein X and Y can be the same or different and are selected from the group consisting of hydrogen, alkyl of from one to six carbon atoms, inclusive, cycloalkyl of five or six carbon atoms, inclusive, phenyl, hydroxyl, alkoxy having from one to three carbon atoms, inclusive, halogen, trifluoromethyl, cyano, carboxyamide and --CO.sub.2 H; Z is selected from the group consisting of hydrogen, alkyl from one to three carbon atoms, inclusive, and phenyl and provided when X is chloro at least one of Y and Z are other than hydrogen consisting of the initial administration of a priming dose (high) and thereafter administering a maintenance (low) dose of from 1/5th to 1/1000th of the priming dose, the maintenance doses being continually administered every 4 to 12 hours or as needed.
    Type: Grant
    Filed: February 4, 1974
    Date of Patent: December 20, 1977
    Assignee: The Upjohn Company
    Inventor: Herbert G. Johnson
  • Patent number: 4048331
    Abstract: A process for inhibiting platelet aggregation by the addition of a member selected from the group consisting of a compound of the formula: ##STR1## wherein Y is lower alkyl of 1 to 8 carbon atoms, cyclopropyl, ethinyl, --CH.sub.3, --F, --Cl, --OCH.sub.3, --OCH.sub.2 OCH.sub.3, --SCH.sub.3, --SCHF.sub.2, --SCH.sub.2 OCH.sub.3, acetyl; R.sub.1 and R.sub.2 are H, CH.sub.3, CHF.sub.2, or taken together are .dbd.CH.sub.2 or .uparw.CF.sub.2 ; and X is hydrogen, lower alkyl of 1 to 8 carbon atoms or a pharmacologically acceptable cation, to in vivo and in vitro platlet systems. In vitro systems include whole blood as kept n blood banks, whole blood as used in heat-lung machines, and platelet rich cocentrates. In vivo systems include human or animal bodies. The process provides a means for treating hemorrhage due to thrombocytopenia which in turn is caused by irradiation, cancer chemotherapy, or immunosuppressants as well as hemophilia due to cogenital defects.
    Type: Grant
    Filed: November 10, 1975
    Date of Patent: September 13, 1977
    Assignee: The Upjohn Company
    Inventor: Neel C. Sekhar
  • Patent number: 4046915
    Abstract: A process for inhibiting platelet aggregation by the addition of a member selected from the group consisting of a compound of the formula: ##STR1## wherein is cyclohexane or phenyl; Y is hydrogen, halogen --CF.sub.3, --OH, lower alkyl of 1 to 8 carbon atoms, lower alkoxy of 1 to 8 carbon atoms, --CN, --NH.sub.2. --SH, or --S-lower alkyl of 1 to 8 carbon atoms; R is hydrogen, lower alkyl of 1 to 8 carbon atoms, inclusive, or a pharmacologically acceptable cation, to in vivo and in vitro platelet systems. In vitro systems include whole blood as kept in blood banks, whole blood as used in heart-lung machines, and platelet-rich concentrates. In vivo systems include human or animal bodies. The process provides a means for treating hemorrhage due to thrombocytopenia which in turn is caused by irradiation, cancer chemotherapy, or immunosuppressants as well as hemophilia due to cogenital defects.
    Type: Grant
    Filed: August 26, 1976
    Date of Patent: September 6, 1977
    Assignee: The Upjohn Company
    Inventor: Neel C. Sekhar
  • Patent number: 4038389
    Abstract: A pharmaceutical vehicle for parenteral administration of medroxyprogesterone acetate is disclosed comprising an aqueous solution of sodium sulfate, quaternary ammonium wetting agent, and a member selected from glycerin, propylene glycol, polyethylene glycol, and polypropylene glycol. The compositions may contain a non-ionic hydrophilic colloid as a preferred adjuvant. Compositions are useful for suspending large amounts, e.g., from 200 to 600 mg./ml. of medroxyprogesterone acetate and maintaining suitable suspendability and syringeability characteristics and are used for the known therapeutic indications for medroxyprogesterone acetate.
    Type: Grant
    Filed: March 29, 1976
    Date of Patent: July 26, 1977
    Assignee: The Upjohn Company
    Inventor: Donald J. Lamb
  • Patent number: 4033816
    Abstract: A process for inhibiting platelet aggregation by the addition of a member selected from the group consisting of a compound of the formula: ##SPC1##Wherein Y is lower alkyl of 1 to 8 carbon atoms, cyclopropyl, ethinyl, --CF.sub.3, --F, --Cl, --OCH.sub.3, --OCHF.sub.3, --OCH.sub.2 OCH.sub.3, --SCH.sub.3, --SCHF.sub.2, --SCH.sub.2 OCH.sub.3, acetyl; R.sub.1 and R.sub.2 are H, CH.sub.3, CHF.sub.2, or taken together are =CH.sub.2 or =CF.sub.2 ; and X is hydrogen, lower alkyl of 1 to 8 carbon atoms or a pharmacolgocially acceptable cation, to in vivo and in vitro platelet systems. In vitro systems include whole blood as kept in blood banks, whole blood as used in heart-lung machines, and platelet rich concentrates. In vivo systems include human or animal bodies. The process provides a means for treating hemorrhage due to thrombocytopenia which in turn is caused by irradiation, cancer chemotherapy, or immunosuppressants as well as hemophilia due to cogenital defects.
    Type: Grant
    Filed: October 15, 1974
    Date of Patent: July 5, 1977
    Assignee: The Upjohn Company
    Inventor: Neel C. Sekhar
  • Patent number: 4025629
    Abstract: Novel p-(trifluoromethylquinolylamino)benzamides are provided, for example, p-[(7-trifluoromethyl-4-quinolyl)-amino]-N,N-(3-methyl-3-azapentamethylene )benzamide and 1-[p-[[7-(trifluoromethyl)-4-quinolyl]amino]benzoyl]piperazine dihydrochloride. Also provided are pharmaceutical dosage unit forms for systemic administration and methods for their systemic administration. The compound, dosage unit forms and methods of systemic administration are useful in obtaining antihypertensive and anti-anxiety effects in mammals.
    Type: Grant
    Filed: March 21, 1975
    Date of Patent: May 24, 1977
    Assignee: The Upjohn Company
    Inventor: Charles E. Coverdale
  • Patent number: 4022904
    Abstract: Pharmaceutical preparations in dosage forms and animal feeds (baits) consisting essentially of compatible, pharmaceutically acceptable carriers, oral and injectable, compounded with a sub-lethal, yet effective, amount of epichlorohydrin for inducing sterility in male mammals. Methods for preventing impregnation of females by male mammals which comprises administering systemically to male mammals a sterilizing amount of epichlorohydrin, also identified as .gamma.-epichlorohydrin.
    Type: Grant
    Filed: December 8, 1975
    Date of Patent: May 10, 1977
    Assignee: The Upjohn Company
    Inventor: Gilbert A. Youngdale
  • Patent number: 4018927
    Abstract: Pharmaceutical compositions for treatment of proliferating skin diseases, primarily psoriasis, but also atopic dermatitis, acne squamous carcinoma of the epidermis, ichthyosis, keratosis. The composition comprises a pharmaceutical carrier with a papaverine alkaloid as the active ingredient of the formula ##STR1## wherein X is carbonyl or (CH.sub.2).sub.n and n is zero or oneR.sub.1 is hydroxy, methoxy, ethoxy or ethylR.sub.2, r.sub.3, and R.sub.4 are hydrogen, hydroxy, methoxy or ethoxyR.sub.5 is hydrogen or ethoxyR.sub.6 is hydrogen or methylAnd R.sub.7 is nothing, hydrogen or methyl and provided that when R.sub.7 is hydrogen or methyl, the double bonds indicated in the A ring are saturated, including the pharmacologically acceptable acid addition salts thereof.The compositions are administered to humans and animals topically and parenterally.
    Type: Grant
    Filed: November 20, 1975
    Date of Patent: April 19, 1977
    Assignee: The Regents of the University of Michigan
    Inventor: John J. Voorhees
  • Patent number: 4014993
    Abstract: A process for inhibiting platelet aggregation by the addition of a member selected from the group consisting of a compound of the formula: ##STR1## WHEREIN IS PHENYL OR CYCLOHEXANE AND X and Y can be the same or different and are hydrogen, fluoro, chloro, bromo, alkyl of from 1 to 8 carbon atoms, inclusive or alkoxy of from 1 to 8 carbon atoms inclusive, and the pharmacologically acceptable salts thereof to in vivo and in vitro platelet systems. In vitro systems include whole blood as kept in blood banks, whole blood as used in heart-lung machines and platelet-rich concentrates. In vivo systems include human or animal bodies. The process provides a means for treating hemorrhage due to thrombocytopenia which in turn is caused by irradiation cancer chemotherapy or immunosuppressants as well as hemophilia due to cogenital defects.
    Type: Grant
    Filed: November 17, 1975
    Date of Patent: March 29, 1977
    Assignee: The Upjohn Company
    Inventor: Neel C. Sekhar
  • Patent number: 4012520
    Abstract: Pharmaceutical preparations in dosage forms and animal feeds (baits) consisting essentially of pharmaceutically acceptable carriers, oral and injectable, compounded with a sublethal, yet effective, amount of a compound having the formula: ##STR1## and R.sub.1 and R.sub.2 are the same or different and are hydrogen, alkyl of from 1 to 17 carbon atoms, alkenyl of from 2 to 17 carbon atoms, phenyl, a heterocyclic ring such as furyl, pyrrolyl, thienyl, indolyl or pyridyl, and R.sub.1 and R.sub.2, taken together, can be a carbocyclic ring of up to 8 carbon atoms, for inducing sterility in male mammals. Methods for preventing impregnation of females by male mammals which comprises administering systemically to male mammals a sterilizing amount of a compound of the Formula l.
    Type: Grant
    Filed: August 4, 1975
    Date of Patent: March 15, 1977
    Assignee: The Upjohn Company
    Inventor: Gilbert A. Youngdale
  • Patent number: 4009282
    Abstract: Pharmaceutical compositions for treatment of proliferating skin diseases, primarily psoriasis. The compositions comprise a pharmaceutical carrier with a prostaglandin of the PGE type including PGE.sub.1, PGE.sub.2, PGE.sub.3, the lower alkyl esters thereof and 13,14-dihydro PGE.sub.1 and alkyl esters thereof as the active ingredient.The compositions are administered to humans and animals topically and parenterally.
    Type: Grant
    Filed: August 25, 1975
    Date of Patent: February 22, 1977
    Assignee: The Regents of the University of Michigan
    Inventor: John J. Voorhees
  • Patent number: 4008217
    Abstract: 1'-Variable-1',1'-dihalo-halobenzeneazomethanes of the structural formula: ##STR1## wherein R is hydrogen; alkyl of from 1 to 7 carbon atoms, inclusive; cycloalkyl of from 3 to 7 carbon atoms, inclusive; haloalkyl of from 1 to 7 carbon atoms, inclusive; halocycloalkyl of from 3 to 7 carbon atoms, inclusive; alkoxyalkyl of from 2 to 8 carbon atoms, inclusive; hydroxyalkyl of from 1 to 7 carbon atoms, inclusive; and phenyl optionally having 1, 2, or 3 substituents, e.g., halogen atoms, lower-alkyl or from 1 to 4 carbon atoms, inclusive, halolower-alkyl of from 1 to 4 carbon atoms, inclusive, and lower-alkoxy of from 1 to 4 carbon atoms, inclusive; the X's are independently bromine, chlorine, or fluorine; m is an integer 0, 1, 2, or 3; and R.sub.1, R.sub.2, and Y are independently halogen, lower-alkyl of from 1 to 4 carbon atoms, inclusive; halolower-alkyl of from 1 to 4 carbon atoms, inclusive; or lower-alkoxy of from 1 to 4 carbon atoms, inclusive; providing however, that at least one R.sub.1 and R.sub.
    Type: Grant
    Filed: November 5, 1975
    Date of Patent: February 15, 1977
    Assignee: The Upjohn Company
    Inventors: Malcolm W. Moon, Victor L. Rizzo
  • Patent number: 4006132
    Abstract: Compounds of the formula: ##STR1## WHEREIN R is alkyl of from 1 to 8 carbon atoms, inclusive; alkoxy of from 1 to 8 carbon atoms, inclusive; haloalkoxy of from 1 to 8 carbon atoms, inclusive; cycloalkyl of from 3 to 8 carbon atoms, inclusive; cycloalkoxy of from 3 to 8 carbon atoms, inclusive; or haloalkyl of from 1 to 8 carbon atoms, inclusive; R' is lower-alkyl of from 1 to 8 carbon atoms, inclusive, phenyl, cycloalkyl of from 3 to 8 carbon atoms, inclusive; or X; X is bromine, chlorine, or fluorine; m is an integer 0 through 5, inclusive, and Y is (independently when m is more than 1) halogen, lower-alkyl of from 1 to 4 carbon atoms, inclusive, lower-alkoxy of from 1 to 4 carbon atoms, inclusive, or halolower-alkyl of from 1 to 4 carbon atoms, inclusive; providing however, that m is 2 to 5 whenever R' is X, and that the sum of the carbon atoms in substituents (Y).sub.m is not more than 15.
    Type: Grant
    Filed: November 14, 1975
    Date of Patent: February 1, 1977
    Assignee: The Upjohn Company
    Inventor: Malcolm W. Moon