Polycarbamic Patents (Class 560/25)
  • Patent number: 5362902
    Abstract: Compounds of formula (I) are diuretic agents for treating various cardiovascular diseases including hypertension, heart failure and renal insufficiency.
    Type: Grant
    Filed: July 21, 1992
    Date of Patent: November 8, 1994
    Assignee: Pfizer Inc.
    Inventors: Ian T. Barnish, Keith James
  • Patent number: 5347034
    Abstract: The present invention relates to an improved process for the production of monomeric and polymeric poly(O-alkylurethanes) of the diphenyl methane series. The process comprises the reaction of the corresponding amines with dialkyl carbonates in the presence of a catalyst, followed by the isolation of the products in a highly pure form. The invention also relates to the use of the produced monomeric and polymeric poly(O-alkylurethanes) for the production of the corresponding isocyanates.
    Type: Grant
    Filed: April 21, 1992
    Date of Patent: September 13, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Hammen, Thomas Schieb, Stefan Wershofen
  • Patent number: 5344830
    Abstract: Diacylpiperazines of general structure ##STR1## are tachykinin receptor antagonists useful in the treatment of inflammatory diseases, pain or migraine, and asthma, and calcium channel blockers useful in the treatment of cardiovascular conditions such as angina, hypertension or ischemia.
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: September 6, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Sander G. Mills, Richard J. Budhu, Conrad P. Dorn, William J. Greenlee, Malcolm MacCoss, Mu T. Wu
  • Patent number: 5342934
    Abstract: The present invention relates to a composition having the general formula: ##STR1## wherein each of A, B, C, X, Y, and Z is independently O, NH, N(CH.sub.2).sub.m CH.sub.3 ], N(C.dbd.O) (CH.sub.2).sub.m CH.sub.3 ], CH.sub.2, S, or Se; each of R.sub.1, R.sub.2, and R.sub.3 is independently phenyl, 4-hydroxyphenyl, pyridyl, pyrrolyl, indolyl, naphthyl, thiophenyl, (C.dbd.O) (CH.sub.2).sub.p CH.sub.3, NH(C.dbd.O) (CH.sub.2).sub.p CH.sub.3 ], OH, COOH, NH.sub.2, or SH; and m, n, and p are integers between 0 and 5. The composition is a chiral receptor molecule useful for the purification of enantiomers of derivatives of amino acids and of compounds able to form hydrogen bonds. The preparation of the composition involves coupling a trifunctional aromatic molecule with three protected chiral molecules at the three aromatic groups, cleaving protecting groups, and joining adjacent chiral groups by multiple lactamizations.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: August 30, 1994
    Assignee: The Trustees of Columbia University in the City of New York
    Inventors: W. Clark Still, Julian A. Simon, Jong-In Hong
  • Patent number: 5340889
    Abstract: Liquid hydroxyurethane products having cyclocarbonate end groups are prepared by reacting a molar excess of a bis-carbonate of a bis-glycidyl ether of neopentyl glycol or 1,4-cyclohexanedimethanol with a polyoxyalkylenediamine such as a polyoxypropylenediamine. These products are useful for the preparation of polyurethanes, polyurethane polyols, polyester polyurethane polyols, and polycarbonate polyurethane polyols.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: August 23, 1994
    Assignee: Texaco Chemical Company
    Inventors: Wheeler C. Crawford, Edward T. Marquis, Howard P. Klein
  • Patent number: 5336566
    Abstract: Compounds are described having the formula: ##STR1## Z represents a cyanuric ring nucleus or the residue of a polyol, L.sub.1, L.sub.2, and L.sub.3 each independently represents a divalent linking group or a covalent bond, andR.sub.1, R.sub.2, and R.sub.3 each independently represents H, alkyl, cycloalkyl, or aryl.These compounds are useful as crosslinking agents for curable compositions such as coating compositions.
    Type: Grant
    Filed: April 30, 1993
    Date of Patent: August 9, 1994
    Assignee: BASF Corporation
    Inventor: John W. Rehfuss
  • Patent number: 5312971
    Abstract: The present invention is directed to a process for the production of polymethylene polyphenyl polyisocyanates by phosgenating the corresponding polyamines in solution in an inert organic solvent, removing excess phosgene, and stripping the solvent. The improvement resides in adding at least 0.02 parts by weight of reducing agent per 150 parts by weight of polyamine to the polyamines at any time prior to the stripping step.
    Type: Grant
    Filed: July 23, 1992
    Date of Patent: May 17, 1994
    Assignee: Miles Inc.
    Inventors: Rick L. Adkins, Clarence D. Blue
  • Patent number: 5312831
    Abstract: The invention relates to novel ureas and urethanes of Formula I: ##STR1## which stimulate cytokine production and may be used to accelerate recovery from neutropenia accompanying radio- or chemotherapy, bone marrow transplantation, or infections. Compounds in the invention or pharmaceutical compositions employing these compounds may be useful in the treatment of cancer, AIDS, aplastic anemia, myelodysplastic syndrome, and infectious diseases, and in the enhancement of immune response.
    Type: Grant
    Filed: May 12, 1993
    Date of Patent: May 17, 1994
    Assignee: American Cyanamid Company
    Inventors: Semiramis Ayral-Kaloustian, Steven R. Schow, Mila T. Du, James J. Gibbons, Jr.
  • Patent number: 5306842
    Abstract: A method for manufacturing a purified aromatic urethane. Aromatic urethanes are synthesized from a N,N'-disubstituted urea and an organic hydroxyl compound in a reaction medium. The organic hydroxyl compound and the primary aromatic amine side product which are present in the reaction mixture is distilled off and removed from the reaction mixture leaving a distillation bottom. The N,N'-disubstituted urea is separated and removed from the distillation bottom by solvent extraction of the aromatic urethane, and the aromatic urethane in the extract phase obtained in said solvent extraction is separated and purified.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 26, 1994
    Assignee: NKK Corporation
    Inventors: Takao Ikariya, Masanori Itagaki, Masatsugu Mizuguchi, Makoto Miyazawa, Sachiko Yamamoto
  • Patent number: 5283352
    Abstract: Catechol compounds of formula I ##STR1## where R.sub.1, R.sub.2, R.sub.3 and X are as described herein are effective Catechol-O-methyltransferase inhibitors.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: February 1, 1994
    Assignee: Orion-yhtyma Oy
    Inventors: Reijo J. Backstrom, Kalevi E. Heinola, Erkki J. Honkanen, Seppo K. Kaakkola, Pekka J. Kairisalo, Inge-Britt Y. Linden, Pekka I. Mannisto, Erkki A. O. Nissinen, Pentti Pohto, Aino K. Pippuri, Jarmo J. Pystynen
  • Patent number: 5272175
    Abstract: The present invention provides substituted tyrosyl diamide compounds of general Formula I: ##STR1## and the pharmaceutically-acceptable salts thereof, which are useful for inducing analgesia in animals, pharmaceutical compositions comprising a pharmaceutically-acceptable carrier and a compound of Formula I, and a method for inducing analgesia in an animal in need thereof comprising administering a therapeutically-effective amount of a compound of Formula I to the animal.
    Type: Grant
    Filed: May 20, 1992
    Date of Patent: December 21, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Donald W. Hansen, Jr., Nizal S. Chandrakumar, Karen B. Peterson, Sofya Tsymbalov, Robert K. Husa
  • Patent number: 5260474
    Abstract: Fungicidal substituted aminophenyl carbamates of the formula ##STR1## in which X represents --CO--NR.sup.8 R.sup.9 ; --CO--OR.sup.9 ; --CO--SR.sup.9 ; --CO--R.sup.10 ; --SO.sub.2 R.sup.9 or hydrogen, in whichR.sup.8 represents hydrogen or alkyl,R.sup.9 represents optionally substituted aryl, optionally substituted aralkyl, optionally substituted alkyl, alkenyl, halogenoalkenyl, or in each case optionally substituted cycloalkyl, cycloalkenyl or cycloalkylalkyl, and R.sup.10 has the meaning of R.sup.9 or represents an optionally substituted heterocyclic ring,Y.sup.1 to Y.sup.4 are identical or different and represent hydrogen, halogen, nitro, cyano, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, alkylsulfonyl or halogenoalkylthio,R.sup.1 to R.sup.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: November 9, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Klaus Sasse, Peter Heitkamper, Klaus Konig, Wilhelm Brandes, Gerd Hanssler, Albrecht Marhold
  • Patent number: 5248748
    Abstract: Disclosed is a diacetylene compound comprising, as structural units, (a) at least one member selected from diacetylene group-containing organic groups of the formulae (I) and (II):R.sup.I --C.tbd.C--C.tbd.C--R.sup.II -- (I)and--R.sup.III --C.tbd.C--C.tbd.C--R.sup.IV -- (II)wherein R.sup.I is hydrogen or a (C1-16) monovalent organic group, and R.sup.II, R.sup.III and R.sup.IV are a (C1-13) divalent organic group,(b) at least one organic group having at least one carbon-to-carbon double bond, and (c) at least one connecting group connecting the units (a) and (b) , which connecting group is selected from amide, imide, ester, ether, amino, imino, urethane, sulfonyl and carbonyl bonds. A cured shaped article made of this compound exhibits isotropically a high elastic modulus and has excellent mechanical properties.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: September 28, 1993
    Assignee: Dir. General of Agency of Industrial Science and Technology
    Inventors: Katsuyuki Nakamura, Satoru Yamazaki, Jinichiro Kato, Kensaku Tokushige
  • Patent number: 5246959
    Abstract: Non-peptidyl compounds characterized generally as poly(aminoalkyl)aminocarbonyl aminoacyl aminodiol derivatives of amino acids are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein X is selected from oxygen atom and methylene; wherein each of R.sub.9 and R.sub.10 is independently selected from hydrido, ethyl and methyl; wherein R.sub.9 and R.sub.10 may be taken together to form a heterocyclic ring having five or six ring atoms and containing one or two nitrogen atoms as ring atoms; wherein each of R.sub.1 and R.sub.2 is independently selected from hydrido, methyl, ethyl and isopropyl; wherein R.sub.3 is selected from benzyl, phenethyl, pyridylmethyl and 2-pyridylethyl; wherein each of R.sub.4 and R.sub.6 is hydrido; wherein R.sub.7 is cyclohexylmethyl; wherein R.sub.8 is selected from ##STR2## with the carbon bearing the hydroxyl radical being in the S configuration; wherein R.sub.
    Type: Grant
    Filed: December 16, 1991
    Date of Patent: September 21, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran
  • Patent number: 5236960
    Abstract: The invention relates to water blown integral skin polyurethane foams made with a particular isocyanate quasi-prepolymer and resin side ingredients to yield a foam having good overall mechanical properties. The isocyanate quasi-prepolymer component of the present invention comprises from 0.5 weight percent to 30.0 weight percent or less uretonimine-carbodiimide-modified diphenylmethane diisocyanate, from 50 weight percent to 80 weight percent 4,4'-diphenylmethane diisocyanate and reacted with from 15 weight percent to 40 weight percent of a polyether polyol containing predominately secondary hydroxyl groups and having an average molecular weight from about 2,000 to 10,000, an average functionality from 1.5 to about 3.2, and a hydroxyl number from about 20 to 60, and optionally with a low molecular weight diol in an amount of from 1.0 weight percent to 10 weight percent, the weight percentages based on the weight of the quasi-prepolymer reactants.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: August 17, 1993
    Assignee: BASF Corporation
    Inventors: Richard P. Harrison, Michael Scarpati, Thirumurti Narayan, Blair J. Zagata
  • Patent number: 5225586
    Abstract: The invention relates to benzocyclobutene capped benzotrifluoride based fluoroaryl ether compounds which are useful in preparing semi-permeable membranes, and films and coatings useful in electronic applications.
    Type: Grant
    Filed: September 13, 1991
    Date of Patent: July 6, 1993
    Assignee: The Dow Chemical Company
    Inventors: Theodore L. Parker, Thomas W. Regulski
  • Patent number: 5223633
    Abstract: A process for the preparation of a compound of the formula ##STR1## which comprises deprotonating a carbamate of the formula ##STR2## in an inert solvent with a selective base, in the presence of a chelate-forming diamine to give a compound of the formula ##STR3## and then reacting III in an inert solvent, either with an achiral electrophile of the formula (IV) or (V) or with an optionally prochiral electrophile of the formula (VI) ##STR4## and in the case in which R.sup.1 represents an electrofugic leaving group, optionally again electrophilically substituted with the formation of an acyl anion and renewed deprotonation, and in a last step, solvolytically removing the protecting group --CO--NR.sup.10 R.sup.11.
    Type: Grant
    Filed: February 19, 1992
    Date of Patent: June 29, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Hoppe, Petra Tebben, Folker Hintze, Thomas Raffel
  • Patent number: 5219975
    Abstract: The present invention is directed to a process for the preparation of amines containing urethane and urea groups. The amines are produced by reacting A) isocyanate prepolymers containing urethane groups and in which the isocyanate groups are reversibly blocked with secondary monoamines with B) amines having molecular weights of from 60 to 500, which are at least difunctional and which have a total of at least two primary or secondary amino groups, with splitting off of the secondary monoamine. The invention is also directed to the amines so produced and to the use as a hardener for an epoxide resin.
    Type: Grant
    Filed: May 7, 1991
    Date of Patent: June 15, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Lutz Schmalstieg, Karl-Heinz Hentschel, Josef Pedain, Klaus Nachtkamp
  • Patent number: 5210274
    Abstract: Ethylenically unsaturated, fluorine-containing urethane derivatives (see Formula I) whose urethane group is substituted on its carboxyl radical by a fluorinated organic radical and on its nitrogen atom by an unfluorinated, ethylenically unsaturated organic radical. Their preparation can be carried out by reacting ethylenically unsaturated, unfluorinated isocyanates with fluorinated organic hydroxyl compounds in bulk in the absence of water or advantageously in inert organic solvents or in ethylenically unsaturated monomers capable of polymerization which behave inertly under the reaction conditions, it being possible to obtain the urethane derivatives directly in liquid or highly viscous or waxy or solid or crystalline form.Urethane derivatives prepared according to the invention are usually readily to very readily soluble in standard nonaqueous, nonpolar inert organic solvents or in various monomers capable of copolymerization.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: May 11, 1993
    Assignee: Hoechst AG
    Inventor: Hans-Ullrich Huth
  • Patent number: 5208236
    Abstract: Novel glutarylamino acid derivative dual inhibitors of neutral endopeptidase and angiotensin converting enzyme of the formula ##STR1## wherein: R.sup.1 and R.sup.3 are independently hydroxy, lower alkoxy, aryllower alkoxy, amino, lower alkylamino and di-(lower alkyl)amino;R.sup.2 is H or hydroxy;R.sup.4 is aryl, substituted aryl, heteroaryl or substituted heteroaryl;R.sup.6 is H or R.sup.7 --(CH.sub.2).sub.3 --, wherein R.sup.7 is amino or (aryllower alkoxy)carbonylamino;Q is --C(O)-- or --SO.sub.2 --;Y is lower alkyl, lower alkoxy, aryllower alkoxy, amino, lower alkylamino, di-(lower alkyl)amino, or a group of the formula ##STR2## wherein A is a bond, --N(R.sup.5)--, or --O--; and R.sup.5 is H or lower alkyl;B is H or Z--(CH.sub.2).sub.m --Z is amino, lower alkylamino, di-(lower alkyl)amino, (aryllower alkoxy)carbonylamino, 1-pyrrolidino or 1-piperidino;m=1,2,3,4 or 5; and n=1,2 or 3; oror a pharmaceutically acceptable addition salt thereof; useful in the treatment of cardiovascular disorders, are disclosed.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: May 4, 1993
    Assignee: Schering Corporation
    Inventor: Bernard R. Neustadt
  • Patent number: 5206412
    Abstract: A selective process for the preparation of diphenylmethane diisocyanate precursors is disclosed. An alkyl phenylcarbamate or an N,N-dialkyl-N'-phenylurea is reacted with a methylene bis(alkyl carbamate) in the presence of an acid catalyst. The use of a staged addition of phenylcarbamate or phenylurea to the methylene bis(carbamate) and the use of a ramped temperature program are the keys to good selectivity to MDI dimer products.
    Type: Grant
    Filed: February 7, 1992
    Date of Patent: April 27, 1993
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Carmen L. Rodriguez, Edward T. Shawl, Haven S. Kesling, Jr.
  • Patent number: 5200494
    Abstract: A one-pack type epoxide composition which has excellent storage stability and which can be rapidly cured at relatively low temperature is provided. It comprises as effective components (A) at least one epoxide having more than one, preferably more than 1.5 epoxy groups per a molecule, and (B) a curing agent prepared by heating and reacting (a) at least one N,N-dialkylaminoalkylamine, (b) at least one amine having one or two nitrogen atoms with active hydrogen and having a ring structure in its molecule, (c) at least one diisocyanate, or (C) a curing agent prepared by heating and reacting (a) at least one N,N-dialkylaminoalkylamine, (b) at least one amine having one or two nitrogen atoms with active hydrogen and having a ring structure in its molecule, (d) at least one epoxide having one or more epoxy groups in a molecule, and (c) at least on diisocyanate.
    Type: Grant
    Filed: April 10, 1991
    Date of Patent: April 6, 1993
    Assignee: Fuji Kasei Kogyo Co., Ltd.
    Inventors: Masao Kubota, Ritaro Nagabuchi, Yasuo Chiba
  • Patent number: 5194660
    Abstract: Processes for producing carbamates comprise contacting a first reactant selected from primary amine components, secondary amine components, urea components and mixtures thereof; carbon monoxide; at least one organic hydroxyl component and at least one oxygen-containing oxidizing agent in the presence of a catalyst composition comprising at least one metal macrocyclic complex, preferably in the further presence of a halogen component.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: March 16, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Tak W. Leung, Bernard D. Dombek
  • Patent number: 5187293
    Abstract: Glycerine derivatives of the formula ##STR1## wherein the residues R.sup.1, R.sup.2 and R.sup.3 have the significance given in the description, and their hydrates, which inhibit blood platelet activating factor (PAF), are described.
    Type: Grant
    Filed: November 19, 1987
    Date of Patent: February 16, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Kaspar Burri, Jean-Marie Cassal, Paul Hadvary, Georges Hirth, Klaus Muller
  • Patent number: 5183927
    Abstract: In preparing an iodoalkynyl carbamate by iodinating an alkynyl carbamate with iodine monochloride in water or a solvent mixture composed of water and an organic solvent in the presence of a base, the iodoalkynyl carbamate can be obtained in a yield of as high as 96 to 98% by using the alkynyl carbamate in a concentration of 5 to 20% by weight, dissolving the iodine monochloride in an aqueous solution of hydrochloric acid or an aqueous solution of an alkali metal chloride (the amount of iodine monochloride used being within the range of 1.0 to 1.2 moles per mole of the alkynyl carbamate and the amount of base used being within the range of 0.95 to 2.00 gram equivalents per mole of iodine monochloride), and carrying out the reaction at a temperature of 10.degree. to 40.degree. C. for a period of 1 to 4 hours.According to this process, highly pure iodoalkynyl carbamates which are useful as industrial germicides can be prepared with good selectivity and in high yield.
    Type: Grant
    Filed: April 15, 1992
    Date of Patent: February 2, 1993
    Assignee: Mitsui Toatsu Chemicals Incorporated
    Inventors: Atsushi Utsunomiya, Mitsuo Nakamura, Toshiaki Kuwatsuka, Yoshinori Tanaka
  • Patent number: 5179223
    Abstract: A process for producing a carbamate is disclosed. In one embodiment, the process comprises contacting a mixture comprising a primary amine component, an urea component and a hydroxy nitrogen component, in particular at least one oxime, at conditions effective to form a carbamate. Certain novel carbamates are also disclosed.
    Type: Grant
    Filed: December 13, 1990
    Date of Patent: January 12, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Tak W. Leung, Donald C. Best, Bernard D. Dombek
  • Patent number: 5175231
    Abstract: A urethane is formed in a new way, without requiring the use of isocyanates. The urethane is formed by reacting a compound containing a plurality of cyclocarbonate groups with a diamine in which the two amine groups have different reactivities with cyclocarbonate, so as to form a urethane oligomer with amine end groups. The urethane oligomer can then be reacted in several different ways to form polyurethane.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: December 29, 1992
    Assignee: Fiber-Cote Corporation
    Inventors: Leonid Rappoport, Roger D. Brown
  • Patent number: 5162405
    Abstract: The present invention comprises novel single-functional and mixtures of multi-functional oligomeric performance additive compounds having one or more components of Structure A R1 ? ? ##STR1## (The definitions of R, Z1, Z2, Z3, A1, A2, A3 and y are given in the Summary Section), their uses and polymeric compounds and compositions containing them which have enhanced oxidative stabilities, enhanced ultraviolet (UV) and light stabilites and/or enhanced flame retardance. An example is the bis sulfonic acid bispotassium salt reaction product from an oligomeric caprolactone diol (TONE.RTM. 260), 2-sulfobenzoic acid anhydride and potassium carbonate, and use of this product, at levels up to about 3.0%, in a general purpose bisphenol A polycarbonate resin, to enhance the fire resistance or flame retardance of the polycarbonate resin.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: November 10, 1992
    Assignee: ELF Atochem North America, Inc.
    Inventors: Ronald E. MacLeay, Jose Sanchez, Daryl L. Stein
  • Patent number: 5144056
    Abstract: The invention relates to fluorinated acrylic monomers of the formula: ##STR1## in which A and W denote divalent linkages, R is a hydrogen atom or a methyl radical, R.sub.F is a perfluoroalkyl radical and Q denotes an oxygen or sulphur atom or the group--NR'--, where R' denotes a hydrogen atom or an alkyl radical. Homo- or copolymers derived from these monomers are useful for the water or oil-repellent treatment of various substrates, particularly leather.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: September 1, 1992
    Assignee: Atochem
    Inventors: Marie-Jose Lina, Andre Dessaint
  • Patent number: 5142056
    Abstract: A retroviral protease inhibiting compound of the formulaA--X--Bor a pharmaceutically acceptable salt, prodrug or ester thereof, wherein X is a linking group; A is(1) substituted amino,(2) substituted carbonyl,(3) functionalized imino,(4) functionalized alkyl,(5) functionalized acyl,(6) functionalized heterocyclic or(7) functionalized (heterocyclic)alkyl; and B is(1) substituted carbonyl independently defined as herein,(2) substituted amino independently defined as herein,(3) functionalized imino independently defined as herein,(4) functionalized alkyl independently defined as herein,(5) functionalized acyl independently defined as herein,(6) functionalized heterocyclic independently defined as herein or(7) functionalized (heterocyclic)alkyl independently defined as herein.
    Type: Grant
    Filed: May 9, 1990
    Date of Patent: August 25, 1992
    Assignee: Abbott Laboratories
    Inventors: Dale J. Kempe, Daniel W. Norbeck, John W. Erickson
  • Patent number: 5130464
    Abstract: A method of manufacturing aromatic urethanes utilizes a urea production process wherein a primary aromatic amine, an aromatic nitro-compound and carbon monoxide are made to react together in the presence of a catalyst and solvents, to produce N,N'-disubstituted urea, the solvlent used in the urea production process consisting at least partly of an amide or oxygen-containing sulfur compound, and having the functions of stabilizing the catalyst and preventing it from separating out in a solution, and of increasing the activity of the catalyst, the quantity of the solvent being sufficient to permit it to fulfill these functions effectively. The method additionally includes an aromatic urethane production process wherein the N,N'-disubstituted urea produced is made to react with an organic compound containing hydroxyl groups, to produce a primary aromatic amine and aromatic urethane, the primary aromatic amine being separated to obtain the aromatic urethane.
    Type: Grant
    Filed: March 16, 1990
    Date of Patent: July 14, 1992
    Assignee: NKK Corporation
    Inventors: Takao Ikariya, Masanori Itagaki, Mikoto Iemoto, Masatsugu Mizuguchi, Tetsuo Hachiya, Tomomichi Nakamura, Makoto Miyazawa, Sachiko Yamamoto
  • Patent number: 5130457
    Abstract: N,N-disubstituted monourethanes and oligourethanes are produced by reacting (a) N-aliphatically and/or N-cycloaliphatically and/or N-araliphatically substituted monourethanes and/or oligourethanes with an alkylating agent in the presence of a solid alkali metal hydroxide. No solvent need by employed but if a solvent is used, that solvent should be an aprotic organic solvent. The alkali metal hydroxide must be used in an equivalent amount. A phase transfer catalyst may optionally be employed. The N,N-disubstituted urethanes obtained by this process are useful in the production of dyes, pharmaceutical products and thermostable synthetic materials.
    Type: Grant
    Filed: March 16, 1987
    Date of Patent: July 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef Sanders, Dieter Dieterich
  • Patent number: 5130454
    Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
  • Patent number: 5126476
    Abstract: A process for making aryl-, heteroaryl-, or cycloalkyl-substituted alkyl urethanes is disclosed. The urethanes are prepared by electrophilic carbamylation of aromatic compounds with alkylene bis(carbamic acid esters) or the equivalent in the presence of an acidic catalyst and a polar aprotic solvent. The alkyl urethanes may be cracked to give the corresponding substituted alkyl isocyanates.
    Type: Grant
    Filed: January 25, 1991
    Date of Patent: June 30, 1992
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Mahmoud K. Faraj, Haven S. Kesling, Jr., John G. Zajacek
  • Patent number: 5120759
    Abstract: Novel compounds of the formula ##STR1## wherein R.sup.1 is lower-alkyl, lower-alkoxy-lower-alkyl, lower-alkylthio-lower-alkyl or furyl, R.sup.2 is lower-alkyl, phenyl-lower-alkyl or cyclohexyl-lower-alkyl, each of R.sup.3 and R.sup.6 independently is hydrogen or fluorine, each of R.sup.4 and R.sup.5 independently is hydrogen or lower-alkoxy or together are methylenedioxy, ethylenedioxy or ethylenoxy and n is an integer from 1 to 3, have a pronounced activity in counteracting cerebral insufficiency or improving cognitive functions and also reduce the multiple-resistance towards cytostatics in the treatment of tumors or of chloroquine resistance in the treatment of malaria. They can accordingly be used as medicaments, especially for the control or prevention of cerebral insufficiency or for the improvement of cognitive functions. The novel compounds of formula I can be manufactured by O-acylating a likewise novel compound of the formula ##STR2## wherein R.sup.
    Type: Grant
    Filed: April 23, 1991
    Date of Patent: June 9, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Urs Hengartner, Henri Ramuz
  • Patent number: 5117036
    Abstract: Aromatic carbamates are selectively and actively prepared by reacting (a) at least one nitroaromatic compound with (b) carbon monoxide and (c) at least one organic compound bearing at least one hydroxyl group, in the presence of:(d) a palladium-based catalyst,(e) at least one coordinate of the formula: ##STR1## in which each of G and G', which may be identical or different, is a bridging group which contains 3 or 4 atoms, at least 2 of which are carbon atoms, with the proviso that G and G' may be linked to each other, and(f) at least one protonic acid in which no proton is linked to a halogen atom, and wherein the amount of palladium present in the reaction medium is less than or equal to 0.01 mole per liter of such reaction medium and the reaction is carried out such that:(i) either the molar ratio (H.sup.+ /Pd) is higher than 150, and/or(ii) the molar ratio (coordinate/Pd) is higher than 20.
    Type: Grant
    Filed: February 23, 1989
    Date of Patent: May 26, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Philippe Leconte, Francois Metz
  • Patent number: 5101062
    Abstract: A process for producing carbamic acid esters (N-phenyl carbamate) which comprises reacting an amino group-containing compound (aniline), oxygen, a nitro group-containing compound (nitrobenzene), a carbon monoxide-containing gas and a hydroxyl group-containing organic compound (ethyl alcohol) in the presence of a compound of a transition metal belonging to Pt group of VIII group (Pd) of the Periodic Table as catalyst, a non-metal halide (HCl) and water.
    Type: Grant
    Filed: September 12, 1989
    Date of Patent: March 31, 1992
    Assignee: Babcock-Hitachi Kabushiki Kaisha
    Inventors: Mutsuo Yamada, Kazumi Murakami, Yasuyuki Nishimura, Fumito Nakajima, Nobuo Matsuo
  • Patent number: 5093412
    Abstract: Macromers for use in preparing stable, low viscosity graft polymer polyols of high solids content are disclosed. These macromers are easily made in high yield with short cycle times, and may be used to prepare graft dispersions containing amine based polyols.
    Type: Grant
    Filed: August 23, 1989
    Date of Patent: March 3, 1992
    Assignee: BASF Corporation
    Inventors: Donald C. Mente, John E. Davis, Steven D. Gagnon, Duane A. Heyman
  • Patent number: 5087727
    Abstract: Azulenesquaric acid dyes of the formula ##STR1## where L is substituted or unsubstituted C.sub.1 -C.sub.12 - alkylene,R.sup.1 is C.sub.1 -C.sub.20 - alkyl, C.sub.5 -C.sub.7 - cycloalkyl or substituted or unsubstituted phenyl andR.sup.2, R.sup.3, and R.sup.5 are each independently of the others hydrogen or substituted or unsubstituted C.sub.1 -C.sub.12 -alkyl,with the proviso that when R.sup.5 is hydrogen the positions of the substituents CH.sub.2 --L--O--CO--NHR.sup.1 and R.sup.4 on an azulene ring may also be interchanged within a ring in either or both of the azulene rings, derived from azulene intermediates that contain urethane groups, are suitable for use in an optical recording medium.
    Type: Grant
    Filed: October 30, 1990
    Date of Patent: February 11, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Schrott, Peter Neumann, Michael Schmitt, Sibylle Brosius, Klaus D. Schomann, Harald Kuppelmaier
  • Patent number: 5087726
    Abstract: This invention relates to novel compounds which are ACAT inhibitors rendering them useful in lowering blood cholesterol levels. The compounds are carbamates represented by the general formula ##STR1## wherein Ar and Ar' represent phenyl or naphthyl each of which may be substituted; m and n each represent zero or one; Z and Y are hydrogen, aliphatic hydrocarbon, heterocyclic, aryl or carbocyclic containing groups.
    Type: Grant
    Filed: February 13, 1990
    Date of Patent: February 11, 1992
    Assignee: Warner-Lambert Company
    Inventors: Patrick M. O'Brien, Drago R. Sliskovic
  • Patent number: 5079383
    Abstract: A process for producing 4,4'-diphenylmethane dicarbamates through one-stage condensation by reacting N-phenyl carbamates with a methylenating agent in presence of a zinc halide, as a catalyst. 4,4'-diphenylmethane dicarbamates can be produced with high selectivity and in high yield.
    Type: Grant
    Filed: July 25, 1990
    Date of Patent: January 7, 1992
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Fujihisa Matsunaga, Mitsuki Yasuhara
  • Patent number: 5075491
    Abstract: A composition useful for incorporation into polymer compositions employed for food packaging or the like comprising a bis- or tris-methine compound having the structural formula ##STR1## wherein A is selected from the radicals ##STR2## wherein R' and R" are each selected from chlorine, bromine, fluorine, alkyl, alkoxy, aryl, aryloxy and arylthio;each n is independently 0, 1, 2;R.sub.1 is selected from a large variety of radicals such as cycloalkyl, phenyl, and straight or branched alkyl which may be substituted;R.sub.2 is alkylene or the like;R.sub.3, R.sub.4, and R.sub.5 are each selected from hydrogen and alkyl; andP and Q and P.sup.1 and Q.sup.1 are selected from cyano, carbalkoxy, carbaryloxy, carbaralkyloxy, or the like.
    Type: Grant
    Filed: December 20, 1989
    Date of Patent: December 24, 1991
    Assignee: Eastman Kodak Company
    Inventors: Max A. Weaver, Wayne P. Pruett, Samuel D. Hilbert
  • Patent number: 5072020
    Abstract: Disclosed is a novel route to diamines and triamines comprising reacting nitroalcohols with isocyanates to prepare di- and trinitro compounds which are subsequently reduced over a metal hydrogenation catalyst to the corresponding polyamino compound.
    Type: Grant
    Filed: March 21, 1990
    Date of Patent: December 10, 1991
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Michael Cuscurida, Wei-Yang Su
  • Patent number: 5068391
    Abstract: The bis-(N-carboalkoxyanilino)methanes, optionally in the presence of at least one alkyl N-phenylcarbamate, are selectively rearranged into methylenedi(phenylurethane), MDU, in the presence of an effective amount of hydrofluoric acid.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: November 26, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Gubelmann, Christophe Rochin, Christian Allandrieu
  • Patent number: 5068250
    Abstract: Compounds such as 1-(4-bromoacetamidobenzyl)-5-methoxy-2-methylindole-3-acetic acid, N-(4-bromoacetamidophenyl) anthranilic acid and N-(3-bromoacetamidophenyl) anthranilic acid function as irreversible ligands for nonsteroidal antiinflammatory drug (NSAID) and prostaglandin binding sites. It is therefore expected that these compounds, and analogs thereof, will have utility as anti-inflammatory drugs, as affinity labeling agents and as ligands for use in affinity chromatography.
    Type: Grant
    Filed: September 29, 1988
    Date of Patent: November 26, 1991
    Assignee: Trustees of University of Pennsylvania
    Inventors: Trevor M. Penning, Leslie J. Askonas
  • Patent number: 5066823
    Abstract: A process for the preparation of 5-acylamino-2,4,6-triiodo or tribromo-benzoic acid derivatives of formula (I), wherein X is I or Br, R is H or a variously substituted alkyl, or a group of formula (II), wherein X has the above meanings; Y is hydroxy, alkoxy, hydroxyalkoxy, alkylamino or hydroxyalkylamino; Z may be the same as COY or it is hydroxylalkylaminocarbonyl provided that at least one of the two acyl or R groups is hydroxy-substituted, which process comprises the rearrangement of the corresponding 5-(alkylaminocarbonyl-alkoxy)-2,4,6-trioodo ro tribromo-benzoic acid derivatives, in the presence of bases.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: November 19, 1991
    Assignee: Bracco Industria Chemica S.p.A.
    Inventors: Ernest Felder, Carlo Musu, Luciano Fumagalli, Fulvio Uggeri
  • Patent number: 5066827
    Abstract: Methylenedi(phenylurethane), MDU, is selectively prepared by condensing an alkyl N-phenylcarbamate with a methylenating agent, e.g., formaldehyde or a precursor thereof, in the presence of a catalytically effective amount of the protonic acid, hydrofluoric acid.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: November 19, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Gubelmann, Christophew Rochin, Christian Allandrieu
  • Patent number: 5019636
    Abstract: A vinyl ether oligomer especially useful for coatings is prepared by reacting an hydroxyl-terminated polyester, a diisocyanate, and a hydroxy monovinyl ether having formulas as defined herein.
    Type: Grant
    Filed: May 10, 1989
    Date of Patent: May 28, 1991
    Assignee: Allied-Signal Inc.
    Inventors: Stephen C. Lapin, James R. Snyder
  • Patent number: 5008435
    Abstract: Process for producing urethanes, by reacting an organic hydroxyl group containing compound and carbon monoxide, either (i) with an organic nitro group containing compound, e.g. nitrobenzene, or (ii) with a primary amine, e.g. aniline, and oxygen, the reacting in both cases being carried out in the presence of a non-noble metal catalyst system comprising a copper catalyst, preferably mixed with a promoter such as a nitrogen or phosphorous containing organic compound for the (i) nitro compound reaction, or an alkali salt for the (ii) amine reaction, e.g. at 200-8000 psig and 100.degree.-300.degree. C., using 0.05-0.4 mole copper catalyst and 0.01-10 moles promoter per mole (i) nitro compound or (ii) amine, and 2-500 moles carbon monoxide, and (in the case of the (ii) amine) 0.5-5 moles oxygen, per mole of the (i) nitro compound or (ii) amine.
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: April 16, 1991
    Assignee: Industrial Technology Research Institute
    Inventors: Kuo-Liang Loh, Puh Shieh, Y. S. Chao, Tsu-Kung Chuang
  • Patent number: RE34137
    Abstract: The present invention relates to a method of manufacturing aromatic urethane, an aromatic mononitro-compound, an aromatic primary amine, and carbon monoxide being reacted using a catalyst containing a platinum group metal-containing compound as a major constituent to prepare N,N'-di-substituted urea. The resultant N,N'-di-substituted urea is reacted with a hydroxyl group-containing organic compound to prepare an aromatic primary amine and aromatic urethane, and the aromatic primary amine is separated to obtain aromatic urethane.
    Type: Grant
    Filed: October 12, 1989
    Date of Patent: December 1, 1992
    Assignee: NKK Corporation
    Inventors: Takao Ikariya, Masanori Itagaki, Masatsugu Mizuguchi, Itaru Sakai, Osamu Tajima