Patents Assigned to The Upjohn Company
  • 4.alpha.,6-Dihydroxy-2.beta.-carboxaldehyde-3.alpha.-tetrahydropyr anacetic acid .gamma.-lactone, 6-alkyl ethers
    Patent number: 4020173
    Abstract: The present specification provides novel intermediates and novel processes for the synthesis of Thromboxane B.sub.2 (11a-homo-11a-oxa-PGF.sub.2.sub..alpha.), its 15-epimer, and various carboxyl derivatives thereof. In particular, there are disclosed various bicyclic tetrahydropyran-containing lactones useful in the above processes, and corresponding acyclic lactones.
    Type: Grant
    Filed: April 14, 1976
    Date of Patent: April 26, 1977
    Assignee: The Upjohn Company
    Inventors: Robert C. Kelly, Norman A. Nelson
  • 1-(.alpha.-Amino-.alpha.-phenyl-o-tolyl)imidazoles
    Patent number: 4020085
    Abstract: 3-Substituted 4-(.alpha.-amino-.alpha.-phenyl-o-tolyl)-4H-1,2,4-triazoles, 2-substituted 1-(.alpha.amino-.alpha.-phenyl-o-tolyl)imidazoles, pharmacologically acceptable acid addition salts thereof and processes for their production. The compounds of this invention and the pharmacologically acceptable acid addition salts thereof are useful as sedatives, hypnotics, anticonvulsants, tranquilizers, and muscle relaxants. They are also useful as feed additives for increasing growth rate and feed efficiency of livestock and poultry.
    Type: Grant
    Filed: April 28, 1976
    Date of Patent: April 26, 1977
    Assignee: The Upjohn Company
    Inventor: Martin Gall
  • Bicyclo [3.1.0]hexane-3-one derivatives of 11-deoxy PGE
    Patent number: 4020097
    Abstract: This invention is a group of 4,5,6-trinor-3,7-inter-m-phenylene prostaglandin-type compounds and processes for making them. These compounds are useful for a variety of pharmacological purposes, including hypotensive control and inhibition of platelet aggregation.
    Type: Grant
    Filed: May 7, 1976
    Date of Patent: April 26, 1977
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Topical clindamycin preparations
    Patent number: 4018918
    Abstract: Disclosed is an anti-inflammatory compound, 6.alpha.,9.alpha.-di-fluoro-11.beta.,17.alpha.,21-trihydroxy-16.beta.-meth ylpregna-1,4-diene-3,20-dione 17,21-diacetate, and topical pharmaceutical formulations which include antimicrobial agents.
    Type: Grant
    Filed: March 19, 1976
    Date of Patent: April 19, 1977
    Assignee: The Upjohn Company
    Inventors: Donald E. Ayer, Carl A. Schlagel, Gordon L. Flynn
  • Intermediate for synthesis of Thromboxane B.sub.2
    Patent number: 4018804
    Abstract: The present specification provides novel intermediates and novel processes for the synthesis of Thromboxane B.sub.2 (11a-homo-11a-oxa-PGF.sub.2), its 15-epimer, and various carboxyl derivatives thereof. In particular, there are disclosed various bicyclic tetrahydrofuran-containing lactones useful in the above processes, and corresponding acyclic lactones.
    Type: Grant
    Filed: April 14, 1976
    Date of Patent: April 19, 1977
    Assignee: The Upjohn Company
    Inventor: William P. Schneider
  • 13,14-Didehydro-PG.sub.3 compounds
    Patent number: 4018803
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
    Type: Grant
    Filed: February 13, 1976
    Date of Patent: April 19, 1977
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Process for the preparation of cycloalkane-1,2-diones
    Patent number: 4018827
    Abstract: Cycloalkanones (C.sub.5-12) are converted to the corresponding 1,2-cycloalkanediones by autoxidation in the presence of a base catalyst (potassium t-butoxide preferred) and a polar organic solvent.
    Type: Grant
    Filed: February 25, 1976
    Date of Patent: April 19, 1977
    Assignee: The Upjohn Company
    Inventors: Durvasula V. Rao, Fred A. Stuber
  • 6-(O-Halophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepine
    Patent number: 4018788
    Abstract: 6-(o-halophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepines of the following formula: ##STR1## wherein the substituent "Hal" is either of the halogens having an atomic number up to 35, inclusive, i.e., fluoro, chloro or bromo, and their pharmacologically acceptable acid addition salts which are especially useful as muscle relaxing and anxiolylic agents.
    Type: Grant
    Filed: December 24, 1975
    Date of Patent: April 19, 1977
    Assignee: The Upjohn Company
    Inventor: Jackson B. Hester, Jr.
  • Method of use, composition, and compounds
    Patent number: 4017540
    Abstract: Certain benzoyl chloride phenylhydrazones have been found to be active against insects and mites. The benzoyl ring and the phenylhydrazone ring can be substituted with a halogen atom, a nitro group, or an alkyl group of from 1 to 6 carbon atoms, inclusive. A new class of pentahalobenzoyl chloride phenylhydrazones is described, particularly pentafluorobenzoyl chloride phenylhydrazones. A further new class of alkylbenzoyl chloride phenylhydrazones, particularly p-toluoyl chloride phenylhydrazones are also described. The compounds are prepared by reacting a benzoic acid phenylhydrazide with phosphorus pentachloride to obtain a benzoyl chloride (dichlorophosphinyl)phenylhydrazone that is reacted with phenol to produce the desired benzoyl chloride phenylhydrazones. Certain of the compounds can be prepared by direct chlorination of a benzaldehyde phenylhydrazone. Methods of use and compositions are described.
    Type: Grant
    Filed: February 22, 1972
    Date of Patent: April 12, 1977
    Assignee: The Upjohn Company
    Inventors: Girts Kaugars, Edwin G. Gemrich, II
  • Organic compounds and process
    Patent number: 4017606
    Abstract: Novel hydrogenated pyrimidine nucleosides and nucleotides are produced by catalytic hydrogenation, particularly in the presence of a rhodium catalyst. The novel compounds are specifically used to inhibit deaminating enzymes, which would inactivate cytosine arabinoside by conversion to uridine arabinoside. Cytosine arabinoside is used for its anti-viral, particularly anti-herpes and anticytotoxic activity in mammals and birds, as well as to destroy phages which interfere with the production of antibiotics. Novel formulations containing cytosine arabinoside and the hydrogenated pyrimidine nucleosides are advantageous to provide prolonged cytosine arabinoside effects.
    Type: Grant
    Filed: March 28, 1975
    Date of Patent: April 12, 1977
    Assignee: The Upjohn Company
    Inventors: Arthur R. Hanze, Gerald W. Camiener
  • Alkyl thio sulfinyl and sulfonyl oxamic compounds, compositions and methods of use
    Patent number: 4017538
    Abstract: It has now been discovered that novel compounds of the figure below and their pharmaceutical compositions are useful in the prophylactic treatment of sensitized humans and animals for allergy and anaphylactic reactions of a reagin or non-reagin mediated nature.
    Type: Grant
    Filed: October 1, 1975
    Date of Patent: April 12, 1977
    Assignee: The Upjohn Company
    Inventors: Charles M. Hall, John B. Wright
  • Substituted tolyl esters of 16-substituted-PGE.sub.2 -type compounds
    Patent number: 4017535
    Abstract: Substituted phenyl and naphthyl esters of PGE.sub.2 analogs, including the 16-alkyl, 16-fluoro, 16-phenoxy, and phenyl-substituted analogs, and their 15-epimers, and their racemic forms, and processes for producing them are disclosed. The products are useful for the same pharmacological and medical purposes as these PGE.sub.2 analogs, and are also useful as a means for obtaining highly purified 16,16-dimethyl-PGE.sub.2, 16-phenoxy-17,18,19,20-tetranor-PGE.sub.2, and 17-phenyl-18,19,20-trinor-PGE.sub.2.
    Type: Grant
    Filed: November 21, 1975
    Date of Patent: April 12, 1977
    Assignee: The Upjohn Company
    Inventor: Walter Morozowich
  • Polyamide-imides
    Patent number: 4017459
    Abstract: Polyamide-imides are described which are derived by conventional procedures from 2,2-bis[4-(p-aminophenoxy)-phenyl]propane (or the corresponding diisocyanate) and trimellitic acid (preferably through the anhydride acid chloride). Copolyamide-imides derived from trimellitic acid, the above diamine (or diisocyanate) and certain other aromatic diamines or diisocyanates (4,4'-diaminodiphenyl ether, m-phenylene diamine and corresponding diisocyanates are preferred) are also described. The above polyamide-imides are engineering thermoplastics which, unlike closely related polyamides and polyimides, can be extruded and injection molded to form parts having good mechanical properties.
    Type: Grant
    Filed: September 19, 1975
    Date of Patent: April 12, 1977
    Assignee: The Upjohn Company
    Inventor: Besir K. Onder
  • As-triazinobenzodiazepin-1-ones
    Patent number: 4017492
    Abstract: Compounds of the formula IV: ##STR1## wherein R.sub.o is hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, --C.sub.n H.sub.2n OR in which n is an integer of 1 to 3, inclusive, and R is hydrogen or methyl, ##STR2## in which n is defined as above, and R.sub.6 and R.sub.7 are hydrogen or alkyl as defined above, or together ##STR3## is pyrrolidino, piperidino, morpholino or ##STR4## in which R.sub.8 is methyl, ethyl, or 2-hydroxyethyl, ##STR5## in which m is an integer of 0 to 3, inclusive, and R.sub.9 is hydrogen, lower alkyl of from 1 to 3 carbon atoms, inclusive, wherein R.sub.1 is hydrogen or methyl; wherein R.sub.2 is phenyl, o-chlorophenyl, o-fluorophenyl, 2,6-difluorophenyl, or 2-pyridyl; and wherein R.sub.3 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro.
    Type: Grant
    Filed: April 2, 1976
    Date of Patent: April 12, 1977
    Assignee: The Upjohn Company
    Inventor: Robert B. Moffett
  • Method of molding articles of polymeric foam substantially free from flashing
    Patent number: 4017572
    Abstract: An improved molding apparatus is described for use with relatively light weight molds, particularly molds for articles having a plurality of voids therein. A light weight two-piece mold, one-half being substantially rigid and the other relatively flexible, is disposed in a jig. The two halves of the mold are held in sealing relationship by inserting a hollow inflatable bag between the exterior of the relatively flexible mold piece and the interior wall of the adjacent jig member and inflating said bag to a pressure superior to that exerted by the expanding foam mix in the mold.The use of the improved apparatus obviates the need for molds of high structural strength (and hence excessive weight) and gives molded articles, particularly those of complex configuration, which are free from flashing.
    Type: Grant
    Filed: April 15, 1975
    Date of Patent: April 12, 1977
    Assignee: The Upjohn Company
    Inventors: Raymond L. Magone, Samir N. Saaty
  • Certain diphenylalkanoamides used as bird and murine repellents
    Patent number: 4017630
    Abstract: Animals, especially birds and murine pests, are repelled by .gamma.- or .omega.-amino-.alpha.,.alpha.-diphenylalkanoamides, their acid addition and quaternary ammonium salts, their N-oxides, and acid addition salts of the N-oxides. The active agents can be coated on grains in order to repel animals especially birds. Animal pest damage to mature crops for harvest and newly planted seeds is prevented.
    Type: Grant
    Filed: November 29, 1974
    Date of Patent: April 12, 1977
    Assignee: The Upjohn Company
    Inventors: Alan J. Lemin, Paul W. O'Connell
  • 9-Deoxy-9,10-didehydro-PGD.sub.1 compounds
    Patent number: 4016184
    Abstract: Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.
    Type: Grant
    Filed: September 17, 1975
    Date of Patent: April 5, 1977
    Assignee: The Upjohn Company
    Inventor: Douglas Ross Morton, Jr.
  • Preparation of polyamide from oligomeric poly-N-carboxylic anhydride
    Patent number: 4016144
    Abstract: Novel oligomeric poly N-carboxylic anhydrides having the following structure are disclosed. ##STR1## The unit Ar represents arylene and x represents an integer from 1 to 10 and y represents a number having an average value from 0 to 4. The polyanhydrides serve as useful storage stable intermediates for the production of polyamides to which they are easily converted by the elimination of carbon dioxide. A process for the preparation of the polyanhydrides from arylene diisocyanates and .alpha.,.omega.-alkylene dicarboxylic acids is disclosed. Processes for the conversion of the polyanhydrides to the corresponding polyamides are also disclosed.
    Type: Grant
    Filed: September 5, 1975
    Date of Patent: April 5, 1977
    Assignee: The Upjohn Company
    Inventor: James N. Tilley
  • Triazino benzodiazepines
    Patent number: 4016165
    Abstract: Compounds of formula IV: ##STR1## wherein R and R.sub.1 are hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.2 is hydrogen or methyl; wherein R.sub.3 is hydrogen, fluoro, chloro, bromo, trifluoromethyl or nitro; and wherein Ar is phenyl, o-chlorophenyl, o-fluorophenyl, 2,6-difluorophenyl or 2-pyridyl, are produced by reacting a hydrazino compound of the formula I ##STR2## wherein R.sub.2, R.sub.3, and Ar are defined as above, with a carbonyl reagent of the formula II: ##STR3## wherein R and R.sub.1 are defined as above and Y is chloro, bromo, iodo or--O--SO.sub.2 --R.sub.4in which R.sub.4 is alkyl, defined as above, phenyl, or tolyl, to give the compound III: ##STR4## wherein R, R.sub.1, R.sub.2, R.sub.3, Ar, and Y are defined as above and heating compound III, in an inert organic solvent, to give compound IV above.
    Type: Grant
    Filed: February 9, 1976
    Date of Patent: April 5, 1977
    Assignee: The Upjohn Company
    Inventor: Robert Bruce Moffett
  • Process for the isolation of polyimides in a solid state
    Patent number: 4016227
    Abstract: A process is described for the isolation, in a solid state, of polyimides particularly those prepared by interaction of a polyisocyanate and a polycarboxylic anhydride in an organic solvent. A solution of the polyimide is passed into water preferably in the form of droplets or as extruded thin strands. The droplets or strands can be chopped, ground or otherwise comminuted after solidification. The process is particularly applicable to the isolation of solvent-soluble polyimides prepared by reaction of benzophenone tetracarboxylic dianhydride with a mixture of methylenebis(phenyl isocyanate) and toluene diisocyanate.
    Type: Grant
    Filed: February 7, 1972
    Date of Patent: April 5, 1977
    Assignee: The Upjohn Company
    Inventors: Gregory L. Lines, Alec Odinak