Alicyclic Carbamates Patents (Class 560/115)
  • Patent number: 5459204
    Abstract: The invention relates to a new polyamine of the following composition: ##STR1## wherein 1.gtoreq.n.gtoreq.6, R represents the hydrocarbon radical of a (cyclo)aliphatic, araliphatic or aromatic diisocyanate having 6-20 C atoms or a trimer thereof andwherein when 2.gtoreq.n.gtoreq.6,R.sup.1 represents an n-valent organic radical such as is formed by removal of n OH groups from a polyhydroxy compound which optionally contains ether oxygen atoms and has an average molecular weight Mn of between 60 and 5,000; andwhen n=1,R.sup.1 represents ##STR2## It furthermore relates to a process for the preparation of a polyamine, in which certain diisocyanates, adducts of diisocyanates with polyols or trimers thereof are reacted with the Schiff base of the following composition: ##STR3## wherein R.sup.2 =H or a branched or unbranched C.sub.1-14 -alkyl radical and R.sup.3 =a branched or unbranched C.sub.1-14 -alkyl radical, an C.sub.1-14 alkyl-substituted phenyl radical or a C.sub.1 -C.sub.
    Type: Grant
    Filed: March 7, 1994
    Date of Patent: October 17, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Rainer Lomoelder, Wilfried Paulen, Felix Schmitt, Elmar Wolf
  • Patent number: 5442087
    Abstract: The invention relates to monomers of the formulaeR.sup.1 --SO.sub.2 --N(CO--OR.sup.2)--R3--O--CO--CR.sup.4 .dbd.CH.sub.2 and R.sup.1 --N(CO--OR.sup.2)--SO.sub.2 --R.sup.3 --O--CO--CR.sup.4 .dbd.CH.sub.2,in which R.sup.1 is a (C.sub.1 -C.sub.20)alkyl, (C.sub.3 -C.sub.10)cycloalkyl, (C.sub.6 -C.sub.14)aryl or (C.sub.7 -C.sub.20) aralkyl radical, individual methylene groups in the radicals containing alkyl being optionally replaced by heteroatoms, R.sup.2 is a (C.sub.3 -C.sub.11)alkyl, (C.sub.3 -C.sub.11 )alkenyl or (C.sub.7 -C.sub.11)aralkyl radical, R.sup.3 is an unsubstituted or substituted (C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.6 -C.sub.4)aryl or (C.sub.7 -C.sub.20)aralkyl radical and R.sup.4 is a hydrogen atom or a methyl group. It further relates to polymers having at least 5 mol % of units with pendent groups of the formula(e) --R.sub.3 --N(CO--OR.sup.2)--SO.sub.2 --R.sup.1 (I) and/or --R.sup.3 --SO.sub.2 --N(CO--OR.sup.2)--R.sup.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: August 15, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Mathias Eichhorn, Gerhard Buhr
  • Patent number: 5411987
    Abstract: Combating fungi with substituted amine acid derivatives of the formula ##STR1## in which R.sup.1 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, cycloalkyl or cycloalkenyl,R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and represent hydrogen, cycloalkyl or alkyl, orR.sup.3 and R.sup.4, together with the carbon atom to which they are bonded, form a cycloalkyl ring, andR.sup.6 represents hydrogen, alkyl, alkenyl, alkinyl, cyanoalkyl, unsubstituted or substituted phenylalkyl, unsubstituted or substituted phenyl or unsubstituted or substituted cycloalkyl, or represents unsubstituted or substituted heterocyclyl or heterocyclylalkyl,orR.sup.5 and R.sup.6, together with the nitrogen atom to which they are bonded, represent a heterocyclyl radical, which can contain further hetero atoms.
    Type: Grant
    Filed: February 25, 1993
    Date of Patent: May 2, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Detlef Wollweber, Thomas Seitz, Wilhelm Brandes
  • Patent number: 5391571
    Abstract: The compounds of the formula: ##STR1## in which R.sup.1 is alkyl of 4 or more carbon atoms, cycloalkyl, 1-adamantyl, 2-adamantyl, 3-noradamantyl, 3-methyl-1-adamantyl, 1-fluorenyl, 9-fluorenyl, cycloalkylalkyl, phenyl, substituted phenyl, alkyl, alkoxy, halo, nitro, cyano or trifluoromethyl, phenylalkyl or substituted phenylalkyl, where the substituent on the benzene ring is alkyl, alkoxy, halo, nitro, cyano, trifluoromethyl or phenyl; R.sup.2 is hydrogen, alkyl or R.sup.1 taken with R.sup.2 and the nitrogen atom to which they are attached form a heterocyclic moiety of the formula: ##STR2## wherein ##STR3## in which R.sup.7 is hydrogen, alkyl, hydroxy, alkanoyloxy, hydroxyalkyl, hydroxycarbonyl, alkoxycarbonyl, phenyl or substituted phenyl, in which the substituent is alkyl, alkoxy, halo, nitro, cyano, haloalkyl, perhaloalkyl or dialkylaminoalkyl; R.sup.8 is hydrogen or alkyl or R.sup.7 and R.sup.8 taken together are polymethylene; R.sup.
    Type: Grant
    Filed: May 13, 1993
    Date of Patent: February 21, 1995
    Assignee: American Home Products Corporation
    Inventors: Richard E. Mewshaw, Thomas J. Commons, Donald P. Strike
  • Patent number: 5391805
    Abstract: An urethane compound is produced in high yield under mild conditions by reacting a formamide compound with dimethyl carbonate in the presence of basic anion exchange resin as a catalyst or by reacting an amine compound with dimethyl carbonate in the presence of basic anion exchange resin as a catalyst and methyl formate. Separation and recovery of the catalyst and purification of the urethane compound can be carried out very readily, and since control of water content is not particularly required in this invention, an amine compound and dimethyl carbonate of poor quality can be used.
    Type: Grant
    Filed: January 28, 1994
    Date of Patent: February 21, 1995
    Assignee: Mitsubishi Gas Chemical Company Inc.
    Inventors: Tomoo Tsujimoto, Takashi Okawa
  • Patent number: 5364961
    Abstract: The invention includes selected novel optically active .alpha.-amino ketones which either are themselves useful or are intermediates for the preparation of known ketomethylene pseudopeptides useful as antibiotics, antibiotic enhancers, or enzyme inhibitors. Further, the present invention provides a method for dehydrogenation/asymmetrical hydrogenation to obtain essentially pure antipodes of ketomethylene pseudopeptides having two chiral centers.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: November 15, 1994
    Assignee: Monsanto Company
    Inventor: John J. Talley
  • Patent number: 5344965
    Abstract: Novel bicyclic alkyl dicarbamates are prepared from norbornadiene and other simple starting materials, and these are subsequently thermally cracked to novel diisocyanate norbornyl derivatives, which are, among others, useful for crosslinking active hydrogen compounds.
    Type: Grant
    Filed: August 20, 1993
    Date of Patent: September 6, 1994
    Assignee: Cytec Technology Corp.
    Inventors: Vazken A. Alexanian, Laurence J. Nummy
  • Patent number: 5344956
    Abstract: The invention provides polymers or copolymers which are prepared by the polymerization of the reaction product of a diisocyanate with a perfluoro compound or an epichlorhydrinadduct thereof and (meth)acrylic esters of a three hydroxyl groups containing compound. Furthermore, the invention relates to fluoroacrylic monomers, a process for preparing the polymers or copolymers and a treatment agent comprising the polymers or copolymers of the invention and an environmentally acceptable solvent. Polymers and copolymers of the invention can be used for making textiles, papers, non-woven articles, leather, plastic, wood, metal, stone and cement water and oil repellent.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: September 6, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Kathy Allewaert, Dirk Coppens, Francecka Fieuws
  • Patent number: 5342981
    Abstract: The present invention relates to intermediates useful in a process for the preparation of a compound of the formula: ##STR1## wherein R.sub.2a is hydrogen or loweralkyl, R.sub.2b is hydrogen, loweralkyl, cycloalkyl or phenyl and R.sub.1 is cycloalkyl, cycloalkylalkyl, phenyl or benzyl. These intermediates are compounds of the formula: ##STR2## wherein P.sub.2 is an O-protecting group, P.sub.3 is an N-protecting group and R.sub.1, R.sub.2a and R.sub.2b are defined as above.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: August 30, 1994
    Assignee: Abbott Laboratories
    Inventors: Daniel J. Plata, Anthony K. L. Fung, Howard E. Morton, Robert Leanna, William R. Baker, John K. Pratt
  • 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: 5322529
    Abstract: Disclosed are liquid alkylphenyl poly(oxypropylene) aminocarbamates which do not form a wax when cooled to -40.degree. C. in a 50 weight percent solution with toluene, said aminocarbamates having at least one basic nitrogen and an average molecular weight of about 600 to 6,000 and wherein the alkyl group is substantially straight-chain of from 25 to 50 carbon atoms. Also disclosed are fuel compositions and concentrates as well as lubricating oil compositions and concentrates containing said alkylphenyl poly(oxypropylene) aminocarbamates.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: June 21, 1994
    Assignee: Chevron Research and Technology Company
    Inventor: Thomas F. Buckley, III
  • Patent number: 5322963
    Abstract: Intermediate compounds (formula [III]and [IV]) useful as starting materials for the synthesis of amino acid derivatives which have renin inhibitory activity and which are useful as remedies for hypertension are prepared stereoselectively in high yield, without requiring complicated process steps. In this method, by reaction of .alpha.-amino aldehyde derivative [I] and compound [II] in the presence of BF.sub.3.OEt.sub.2, as shown in the following reaction formula, .alpha.-amino-.beta.-hydroxy-.delta.-ketone derivative [III] is prepared, and furthermore, by reducing it as required, compound [IV] is obtained: ##STR1## (where R.sup.1 is a protective group on the amino group, R.sup.2 is a lower alkyl group which may be branched, and R.sup.4 is a cyclohexyl group or phenyl group).
    Type: Grant
    Filed: October 5, 1992
    Date of Patent: June 21, 1994
    Assignee: Japan Tobacco, Inc.
    Inventors: Saizo Shibata, Eiji Shirakawa, Yasuki Yamada, Koji Ando, Itsuo Uchida
  • Patent number: 5318989
    Abstract: The present invention relates to a novel and efficient process for the preparation of 8-hydroxybicyclo[7.3.1]tridec-4-ene-2,6-diyne ring system which is part of the aglycone of esperemicin and to novel cytotoxic antitumor agents having said bicyclic ring system. The present invention also provides a method for treating mammalian malignant tumors by administering to an animal in need of such treatment an antitumor effective amount of a compound of the present invention.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: June 7, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventors: John F. Kadow, Mark D. Wittman
  • 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: 5302717
    Abstract: The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and a hydrocarbyl halide. The amine or alcohol is reacted with carbon dioxide in a suitable solvent system and in the presence of a base selected from the group consisting of a phosphazene compound and a mixture of a phosphazene compound and an organic, nitrogenous base, to form the ammonium carbamate or carbonate salt which is then reacted in a polar aprotic solvent with a hydrocarbyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: April 12, 1994
    Assignee: Monsanto Company
    Inventors: William D. McGhee, John J. Talley
  • Patent number: 5300678
    Abstract: A process for the preparation of a .omega.-(O-substituted urethano)alkylcarboxylate, wherein a lactam having from 4 to 9 ring members, which can have alkyl, alkenyl, cycloalkyl, or aralkyl groups containing up to 12 carbon atoms as substituents, is reacted with a carbonic diester of an alkanol, alkenol, cycloalkanol, or aralkanol containing up to 16 carbon atoms, at a temperature of from 25.degree. to 300.degree. C. in the presence of a catalytically effective amount of a base.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: April 5, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Martin Brudermueller
  • Patent number: 5298651
    Abstract: A process for preparing isocyanates comprising (a) contacting carbon dioxide and a primary amine in the presence of an aprotic organic solvent and a phosphazene compound or a mixture of a phosphazene compound and an organic, nitrogenous base selected from the group consisting of guanidine compounds, amidine compounds, tertiary amines, pyridine and mixtures thereof to produce the corresponding ammonium carbamate salt, and (b) reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent to produce the corresponding isocyanate. A second embodiment comprises recovering the ammonium carbamate salt of step (a) prior to reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent in the presence of an aprotic organic solvent and a phosphazene compound or a mixture of a phosphazene compound and an organic, nitrogenous base selected from the group consisting of guanidine compounds, amidine compounds, tertiary amines, pyridine and mixtures thereof.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: March 29, 1994
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Thomas E. Waldman
  • Patent number: 5298505
    Abstract: Compounds characterized generally as ethynyl alanine amino diol compounds having a piperazinyl-terminated or a piperazinyl-alkylamino-terminated group and derivatives thereof are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are those of Formula I ##STR1## wherein A is selected from CO and SO.sub.2 ; wherein X is selected from oxygen atom and methylene; wherein G is a piperazinyl group or is a piperazinyl-containing group of Formula II: ##STR2## wherein B is a piperazinyl group or a alkylene-bridged-piperazinyl group; wherein R.sub.1 is selected from hydrido, methyl, ethyl, isopropyl and n-propyl; wherein R.sub.2 is phenylmethyl; wherein each of R.sub.3 and R.sub.5 is hydrido; wherein R.sub.4 is selected from ##STR3## wherein V is selected from hydrido and methyl; wherein R.sub.6 is cyclohexylmethyl; wherein R.sub.
    Type: Grant
    Filed: August 14, 1992
    Date of Patent: March 29, 1994
    Assignee: G. D. Searle & Co.
    Inventor: Gunnar J. Hanson
  • Patent number: 5292925
    Abstract: N-t-butyloxycarbonyl-3-cyclohexyl-L-alanine methyl ester, previously known only as an oil, is provided in crystalline form. By addition of an organic solvent, such as methanol and/or n-hexane, to the ester in the form of an oil and cooling, crystals may be obtained. Alternatively, the ester in oily form may be seeded with a crystal produced previously. The crystalline material is of higher purity than the previously known oils, and is more useful than the oils as an intermediate in the pharmaceutical industry.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: March 8, 1994
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masahiko Kurauchi, Tohru Nakamura
  • Patent number: 5286897
    Abstract: N-t-butyloxycarbonyl-3-cyclohexyl-L-alanine methyl ester, previously known only as an oil, is provided in crystalline form. By addition of an organic solvent, such as methanol and/or n-hexane, to the ester in the form of an oil and cooling, crystals may be obtained. Alternatively, the ester in oily form may be seeded with a crystal produced previously. The crystalline material is of higher purity than the previously known oils, and is more useful than the oils as an intermediate in the pharmaceutical industry.
    Type: Grant
    Filed: August 3, 1992
    Date of Patent: February 15, 1994
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masahiko Kurauchi, Tohru Nakamura
  • Patent number: 5227401
    Abstract: Compounds characterized generally as ethynyl alanine amino diol derivatives are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are those of Formula I ##STR1## wherein A is selected from CO and SO.sub.2 wherein X is selected from oxygen atom and methylene; wherein each of R.sub.1 and R.sub.9 is a group independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, benzyl, .beta.,.beta.,.beta.-trifluoroethyl, t-butyloxycarbonyl and methoxymethylcarbonyl, and wherein the nitrogen atom to which R.sub.1 and R.sub.9 are attached may be combined with oxygen to form an N-oxide; wherein R.sub.2 is selected from hydrido, methyl, ethyl and isopropyl; wherein R.sub.3 is selected from benzyl, cyclohexylmethyl, phenethyl, imidazolemethyl, pyridylmethyl and 2-pyridylethyl; wherein R.sub.5 is propargyl or a propargyl-containing moiety; wherein R.sub.7 is cyclohexylmethyl; wherein each of R.sub.4 and R.sub.6 is independently selected from hydrido and methyl; wherein R.
    Type: Grant
    Filed: October 29, 1991
    Date of Patent: July 13, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran
  • Patent number: 5223535
    Abstract: Compounds characterized generally as propargyl glycine amino propargyl diol derivatives are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are those of Formula I ##STR1## wherein A is selected from CO and SO.sub.2 wherein X is selected from oxygen atom and methylene; wherein each of R.sub.1 and R.sub.9 is a group independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, benzyl, .beta.,.beta.,.beta.-trifluoroethyl, t-butyloxycarbonyl and methoxymethylcarbonyl, and wherein the nitrogen atom to which R.sub.1 and R.sub.9 are attached may be combined with oxygen to form an N-oxide; wherein R.sub.2 is selected from hydrido, methyl, ethyl and isopropyl; wherein R.sub.3 is selected from benzyl, cyclohexylmethyl, phenethyl, imidazolemethyl, pyridylmethyl and 2-pyridylethyl; wherein each of R.sub.5 and R.sub.8 is independently propargyl or a propargyl-containing moiety; wherein R.sub.7 is cyclohexylmethyl; wherein each of R.sub.4 and R.sub.
    Type: Grant
    Filed: October 29, 1991
    Date of Patent: June 29, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran
  • Patent number: 5223638
    Abstract: The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and a hydrocarbyl halide. The amine or alcohol is reacted with carbon dioxide in a suitable solvent system and in the presence of an amidine or guanidine base, to form the ammonium carbamate or carbonate salt which is then reacted in a polar aprotic solvent with a hydrocarbyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: June 29, 1993
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Barry L. Parnas, Dennis P. Riley, John J. Talley
  • Patent number: 5221788
    Abstract: A polyurethane polyol obtained by reacting a hydrocarbon diol of the formula (A):HO--R--OH (A)wherein R is a C.sub.7-20 linear or branched alkylene group, with isophorone diisocyanate and having a number average molecular weight of from 500 to 20,000.
    Type: Grant
    Filed: September 3, 1992
    Date of Patent: June 22, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Junichi Goto, Takayuki Ohta
  • 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: 5214129
    Abstract: A renin inhibiting compound of the formula: ##STR1## wherein A is a substituent; W is C.dbd.O or CHOH; U is CH.sub.2 or NR.sub.2, provided that when W is CHOH then U is CH.sub.2 ; R.sub.1 is loweralkyl, cycloalkylmethyl, benzyl, 4-methoxybenzyl, halobenzyl, (1-naphthyl)methyl, (2-naphthyl)methyl, (4-imidazoyl)methyl, .alpha.,.alpha.-dimethylbenzyl, 1-benzyloxyethyl, phenethyl, phenoxy, thiophenoxy or anilino; R.sub.2 is hydrogen or loweralkyl; R.sub.3 is loweralkyl, [(alkoxy)alkoxy]alkyl, (thioalkoxy)alkyl, loweralkenyl, benzyl or heterocyclic ring substituted methyl; R.sub.4 is loweralkyl, cycloalkylmethyl or benzyl; R.sub.5 is vinyl, formyl, hydroxymethyl or hydrogen; R.sub.7 is hydrogen or loweralkyl; R.sub.8 and R.sub.9 are independently selected from OH and NH.sub.2 ; and R.sub.6 is hydrogen, loweralkyl, vinyl or arylalkyl; provided that when R.sub.5 and R.sub.7 are both hydrogen and R.sub.8 and R.sub.9 are OH, the carbon bearing R.sub.5 is of the "R" configuration and the carbon bearing R.sub.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: May 25, 1993
    Assignee: Abbott Laboratories
    Inventors: Jay R. Luly, Jacob J. Plattner, Dale J. Kempf
  • Patent number: 5214169
    Abstract: The present invention as directed to a new class of N-(2,3-epoxycyclopentyl) carbamate derivatives as described by Formula V below, that are useful as chemical intermediates in the production of a new class of anti-hypertensives: ##STR1##
    Type: Grant
    Filed: April 30, 1992
    Date of Patent: May 25, 1993
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventor: Theophilus F. Leapheart
  • 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: 5202483
    Abstract: Ethylenically unsaturated compounds of the general formula I ##STR1## where R.sub.1 is alkyl of 1 to 4 carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, phenyl or phenyl in which some or all of the hydrogen atoms have been replaced by radicals R.sup.4, not more than two substituents R.sup.4 being identical, or R.sup.1 together with R.sup.2 or together with R.sup.6 forms a --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 -- bridge,R.sup.4 is alkyl of 1 to 24 carbon atoms, --OH, --O--R.sup.7, --S--R.sup.7, ##STR2## R.sup.2 or R.sup.6, independently of one another, both are hydrogen, or one of the radicals R.sup.4, or, where R.sup.1 is aryl,R.sup.2 or R.sup.6 is a direct bond to R.sup.1 in the ortho-position with respect to the carbonyl group, andR.sup.3 and R.sup.5 are each hydrogen, one of the radicals R.sup.4 or a group the general formula II ##STR3## where R.sup.7 and R.sup.8 are each alkyl of 1 to 4 carbon atoms,R.sup.9 is cycloalkyl of 5 or 6 carbon atoms,R.sup.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: April 13, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Rehmer, Kaspar Bott
  • Patent number: 5200547
    Abstract: The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and an allyl halide. The amine or alcohol is reacted with carbon dioxide to form the ammonium carbamate or carbonate salt which is then reacted with a palladium tertiary phosphine catalyst complex of an allyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: April 6, 1993
    Assignee: Monsanto Company
    Inventors: Dennis P. Riley, William D. McGhee
  • 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: 5191104
    Abstract: This invention relates to a process for the alkoxylation of a carboxylated compound comprising contacting the carboxylated compound with an alkylene oxide in the presence of a mixed metal oxide catalyst or a modified bimetallic or polymetallic catalyst under conditions effective to alkoxylate the carboxylated compound.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: March 2, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5191032
    Abstract: A heterofunctional macromer represented by the formula: ##STR1## in which R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; R.sub.2 is a (poly) lactone or (poly) ether chain;X.sub.1 is --COO--, --COOCH.sub.2 CH.sub.2 OCO--, --CONHCOO--, --COOCH.sub.2 CH.sub.2 NH--COO-- or ##STR2## X.sub.2 is --O--, --COO-- or --OCO--NH--R.sub.3 --NHCOO-- group; R.sub.3 is C.sub.1 -C.sub.6 alkylene, aromatic or alicyclic group;A is --CH.sub.2 --, --C(CH.sub.3).sub.2 -- or ##STR3## group; and reactive polymers derived from said macromer.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: March 2, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kei Aoki
  • Patent number: 5189135
    Abstract: Low molecular weight non-film forming fluorinated polyurethanes having a hydroxy functionality obtained from the reaction of at least one diisocyanate with at least one hydroxy-capped perfluoropolyether having a molecular weight within the range of from greater than 1,000 to 5,000 and with at least one polyol with a functionality of at least 2.
    Type: Grant
    Filed: May 5, 1992
    Date of Patent: February 23, 1993
    Assignee: Syremont S.p.A.
    Inventors: Ennio Cozzi, Franco Federici, Paolo Parrini
  • 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: 5177109
    Abstract: Compounds, compositions and methods are described for treating a CNS disorder such as a cognitive disorder, epilepsy, depression, Parkinson's disease, Alzheimer's disease, a neurodegenerative disease or neurotoxic injury. Compound of interest are 2-amino-4,5-methyleneadipic acid compounds and derivatives defined by the formula I: ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, ##STR2## with each of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein each of X and Y is independently selected from hydroxyl, alkoxy, alkylthio, amino and ##STR3## with each of R.sup.6 and R.sup.7 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein any of R.sup.1 through R.sup.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: January 5, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Roberto Pellicciari, Benedetto Natalini, Maura Marinozzi, Alexis A. Cordi, Joseph B. Monahan, Thomas H. Lanthorn
  • 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: 5134161
    Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 is lower alkoxy or optionally substituted phenoxy,R.sup.2 is the same as R.sup.1, or R.sup.2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl,R.sup.3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2;both X groups are the same and X is either --C(O)OR.sup.4 or --C(O)NR.sup.5 R.sup.6, whereinR.sup.4 is alkyl, phenyl or benzyl optionally substituted with one or two lower alkyl groups, lower alkoxy groups or halo; andR.sup.5 and R.sup.6 are independently hydrogen, lower alkyl, cycloalkyl or phenyl optionally substituted with one or two lower alkyl groups, lower alkoxy groups or halo.
    Type: Grant
    Filed: April 15, 1988
    Date of Patent: July 28, 1992
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Michael C. Venuti, John M. Young
  • Patent number: 5130468
    Abstract: A process and intermediates useful for the preparation of (E)-alkene dipeptide isosteres are disclosed.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: July 14, 1992
    Assignee: Abbott Laboratories
    Inventor: Dale J. Kempf
  • 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: 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: 5112859
    Abstract: The compounds of the formula: ##STR1## in which R.sup.1 is hydrogen or alkyl; R.sup.2 is alkyl, cycloalkyl, cycloalkylalkyl, phenylalkyl or alkylphenylalkyl; or R.sup.1 and R.sup.2 taken together complete a heterocyclic moiety of the formula: ##STR2## in which X is ##STR3## NR.sup.5,--O-- or --S--; where R.sup.3, R.sup.4 and R.sup.5 are, independently hydrogen, alkyl, phenyl or substituted phenyl, in which the substituents are halogeno, alkoxy or trifluoromethyl; R.sup.6 is hydrogen, alkyl of gemdialkyl and n is one of the integers 0, 1 or 2, are cholesterol ester hydrolase inhibitors useful in the treatment of high serum cholesterol levels and associated disease states in the mammal such as coronary heart disease, atherosclerosis, familial hypercholesterolemia, hyperlipemia, and the like.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: May 12, 1992
    Assignee: American Home Products Corporation
    Inventors: Thomas J. Commons, Richard E. Mewshaw, Donald P. Strike
  • Patent number: 5108653
    Abstract: Disclosed are surface-active polycarbodiimides containing a hydrophilic portion and a hydrophobic portion joined through the reaction of a carbodiimide group with a reactive functional group. The surface-active polycarbodiimides may be linear or branched, monodisperse or polydisperse, but preferably are of the branched, monodisperse type. The surface-active polycarbodiimides are useful as surfactants, and are particularly useful as emulsifiers in cross-linkable, carboxyl-containing resin systems, such as aqueous latexes.
    Type: Grant
    Filed: June 12, 1991
    Date of Patent: April 28, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: James W. Taylor
  • Patent number: 5099058
    Abstract: The present invention relates to N,N-disubstituted compounds containing urethane groups and terminal hydroxyl groups corresponding to the general formula ##STR1## wherein X is the residue of a strong memobasic or polybasic acid remaining after dissociation of the proton or protons of said acid or a hydroxyl group;Y is an n-functional hydrocarbon group having a molecular weight of from about 15 to about 8000 (preferably from about 300 to about 4000) and optionally interrupted by oxygen, sulfur, or silicon atoms, or by ester, carbonate, urea, N-monosubstituted urethane, or N,N-disubstituted urethane groups;1.sub.R hydrogen or a hydrocarbon group having a molecular weight of from about 15 to about 200;2.sub.R is the radical of an alkylating or arylating agent; and is an integer of from 2 to about 6.The present invention further relates to a process for preparing such compounds and to a method for using such compounds in the production of plastics.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: March 24, 1992
    Inventors: Josef Sanders, Dieter Dieterich
  • Patent number: 5091556
    Abstract: A process for preparing carbamates is disclosed, in which:a stoichiometric or higher-than-stoichiometric amount of an alkyl carbonate or a cycloalkyl carbonate is reacted with an aliphatic, cycloaliphatic or aromatic amine, in a first reaction step, by operating in the presence of a carbamation catalyst, in order to produce a mixture of a carbamate and an urea,the urea contained in the reaction product from the first process step is reacted with carbonate, in a second reaction step, in order to produce the corresponding carbamate, andthe reaction mixture coming from the second process step is submitted to treatments in order to recover the carbamate.The process makes it possible high yields and high values of selectivity to the useful reaction product to be obtained.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: February 25, 1992
    Assignee: Enichem Synthesis, S.p.A.
    Inventors: Carlo Calderoni, Franco Mizia, Franco Rivetti, Ugo Romano
  • Patent number: 5091575
    Abstract: A renin inhibiting compound of the formula: ##STR1## wherein A is a substituent; W is C.dbd.O or CHOH; U is CH.sub.2 or NR.sup.2, provided that when W is CHOH then U is CH.sub.2 ; R.sub.1 is loweralkyl, cycloalkylmethyl, benzyl, 4-methoxybenzyl, halobenzyl, (1-naphthyl)methyl, (2-naphthyl)methyl, (4-imidazoyl)methyl, .alpha.,.alpha.-dimethylbenzyl, 1-benzyloxyethyl; phenethyl, phenoxy, thiophenoxy or anilino; R.sub.2 is hydrogen or loweralkyl; R.sub.3 is loweralkyl, [(alkoxy)alkoxy]alkyl, (thioalkoxy)alkyl; lowerakenyl, benzyl or heterocyclic ring substituted methyl; R.sub.4 is loweralkyl, cycloalkylmethyl or benzyl; R.sub.5 is vinyl, formyl, hydroxymethyl or hydrogen; R.sub.7 is hydrogen or loweralkyl; R.sub.8 and R.sub.9 are independently selected from OH and NH.sub.2 ; and R.sub.6 is hydrogen, loweralkyl, vinyl or arylalkyl; provided that when R.sub.5 and R.sub.7 are both hydrogen and R.sub.8 and R.sub.9 are OH, the carbon bearing R.sub.5 is of the "R" configuration and the carbon bearing R.sub.
    Type: Grant
    Filed: June 10, 1991
    Date of Patent: February 25, 1992
    Assignee: Abbott Laboratories
    Inventors: Jay R. Luly, Jacob J. Plattner, Dale J. Kempf
  • Patent number: 5091531
    Abstract: Compounds of general formula (I) ##STR1## wherein R.sup.1 represents an optinally substituted carbocyclic or heterocyclic aryl group, or an optionally substituted alkyl, alkenyl, cycloalkyl or cycloalkenyl group; R.sup.2 represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl group or an optionally substituted carbocyclic or heterocyclic aryl or aralkyl group; R.sup.3 represents a hydrogen atom or an alkyl group; and either X represents an oxygen or sulphur atom, a group --CH.sub.2 -- or a group NR.sup.4 where R.sup.4 represents a hydrogen atom or a C.sub.1-4 alkyl group; and Y represents a group --CH.sub.2 -- or --CH.sub.2 CH.sub.2 -- X-Y together represent the group --CH.dbd.CH--; and salts and physiologically functional derivatives thereof are useful in the treatment of tumours. Processes for preparing the compounds, intermediates useful in their preparation, pharmaceutical compositions containing them and their use in the treatment of tumours are also described.
    Type: Grant
    Filed: August 12, 1988
    Date of Patent: February 25, 1992
    Assignee: Burroughs Wellcome Co.
    Inventor: Simon T. Hodgson