Nitrogen, Except As Nitro Or Nitroso, Attached Indirectly To The Cyano Group By Nonionic Bonding Patents (Class 558/408)
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Patent number: 6165237Abstract: Compounds of the general formula IZ--CH.sub.2 --NY.sub.2-n H.sub.n (I)wheren is 0 or 1,z is a straight-chain or branched polyalkyl radical having a number average molecular weight of from about 150 to 40,000, andY is a radical of the formula IIa or IIb ##STR1## where the radicals R, R.sup.1 and R.sup.2 independently of one another, are each hydrogen, an unsubstituted or substituted alkyl, alkenyl or alkynyl radical or an unsubstituted or substituted cycloalkyl, aryl or arylalkyl radical, which may carry one or more heteroatoms, andA is an alkyleneimine radical; or, ifn is 0, one of the radicals Y may be a polyoxyalkylene radical, and processes for their preparation and fuel and lubricant compositions, and mixtures of additives, which contain the novel compounds.Type: GrantFiled: August 17, 1998Date of Patent: December 26, 2000Assignee: BASF AktiengesellschaftInventors: Manfred Julius, Roland Ettl, Wolfgang Gunther, Thomas Greindl
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Patent number: 6063953Abstract: Disclosed are novel high-sensitivity positive- and negative-working chemical-sensitization photoresist compositions capable of giving a highly heat-resistant patterned resist layer of high resolution having excellently orthogonal cross sectional profile without being influenced by standing waves. The composition contains, as an acid generating agent by irradiation with actinic rays, a specific cyano-substituted oximesulfonate compound such as .alpha.-(methylsulfonyloxyimino)-4-methoxybenzyl cyanide. The advantages obtained by the use of this specific acid-generating agent is remarkable when the film-forming resinous ingredient has such a molecular weight distribution that the ratio of the weight-average molecular weight to the number-average molecular weight does not exceed 3.5.Type: GrantFiled: January 26, 1999Date of Patent: May 16, 2000Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Hiroyuki Yamazaki, Yoshiki Sugeta, Hiroshi Komano
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Patent number: 6020515Abstract: A novel process for the preparation of malononitrile which involves subjecting a (2-cyano-N-alkoxy)acetimidoyl halide to a high-temperature treatment.Type: GrantFiled: March 19, 1999Date of Patent: February 1, 2000Assignee: Lonza, Ltd.Inventors: Peter Chen, Johannes Hoffner, Andre Mueller, Rudolf Fuchs
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Patent number: 6004724Abstract: New oximsulfonate compounds of the formulae I or II, ##STR1## wherein m is 0 or 1; x is 1 or 2; R.sub.1 is, for example phenyl, which is unsubstituted or substituted or R.sub.1 is a heteroaryl radical that is unsubstituted or substituted, or, if m is 0, R.sub.1 additionally is C.sub.2 -C.sub.6 alkoxycarbonyl, phenoxycarbonyl or CN; R'.sub.1 is for example C.sub.2 -C.sub.12 alkylene, phenylene; R.sub.2 has for example one of the meanings of R.sub.1 ; n is 1 or 2; R.sub.3 is for example C.sub.1 -C.sub.18 alkyl, R'.sub.3 when x is 1, has one of the meanings given for R.sub.3, or R'.sub.3 in the formula IV and when x is 2 in the formula 1, is for example C.sub.2 -C.sub.12 alkylene, phenylene; R.sub.4 and R.sub.5 are independently of each other for example hydrogen, halogen, C.sub.1 -C.sub.6 alkyl; R.sub.6 is for example hydrogen, phenyl; R.sub.7 and R.sub.8 are independently of each other for example hydrogen or C.sub.1 -C.sub.12 -alkyl; R.sub.9 is for example C.sub.1 -C.sub.12 alkyl; A is S, O, NR.sub.Type: GrantFiled: June 25, 1998Date of Patent: December 21, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Hitoshi Yamato, Hartmut Bleier, Jean-Luc Birbaum, Martin Kunz, Kurt Dietliker, Christoph De Leo, Toshikage Asakura
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Patent number: 5968978Abstract: Compounds of the formula I ##STR1## in which the symbols have the meanings indicated in the claims, have outstanding antiarrhythmic properties. They exhibit a cardioprotective component. They can inhibit or greatly decrease, in a preventive manner, the pathophysiological processes in the formation of ischemically induced damage, in particular in the elicitation of ischemically induced cardiac arrhythmias. Moreover, they have a strong inhibitory action on the proliferation of cells.Type: GrantFiled: September 21, 1998Date of Patent: October 19, 1999Assignee: Hoechst Marion Roussel DeutschlandInventors: Heinz-Werner Kleemann, Jan-Robert Schwark, Sabine Faber, Hans Jochen Lang, Andreas Weichert, Hans-Willi Jansen
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Patent number: 5932766Abstract: The present invention discloses a process for the preparation of a compound having formula 4: ##STR1## The process comprises the step of reacting an enolate having the formula: ##STR2## with a Grignard reagent. The enolate salt is formed in situ from the reaction of a protected ester wherein M is an alkali metal. R.sub.6 and R.sub.7 are each hydrogen or are independently selected from ##STR3## wherein R.sub.a and R.sub.b are independently selected from hydrogen, lower alkyl and phenyl and R.sub.c, R.sub.d and R.sub.e are independently selected from hydrogen, lower alkyl, trifluoromethyl, alkoxy, halo and phenyl; and ##STR4## wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from lower alkyl, trifluoromethyl, alkoxy and halo. Alternatively, R.sub.6 is as defined above and R.sub.7 is R.sub.12 OC(O)-- wherein R.sub.12 is benzyl; or R.sub.6 and R.sub.7 taken together with the nitrogen atom to which they are bonded form ##STR5## wherein R.sub.Type: GrantFiled: May 30, 1997Date of Patent: August 3, 1999Assignee: Abbott LaboratoriesInventors: Anthony R. Haight, Timothy L. Stuk, Jerome A. Menzia
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Patent number: 5859279Abstract: A process for the preparation of a compound of formula (VI), optionally in enantiomerically-enriched form (R or S), comprises chemoselective reduction of a novel compound of formula (V), wherein Ar.sup.1 and Ar.sup.2 are independently selected from optionally-substituted aromatic or heteroaromatic groups having upto 20 C atoms, Ak is C.sub.1-20 alkyl, and R is H or C.sub.1-20 alkyl.Type: GrantFiled: September 10, 1997Date of Patent: January 12, 1999Assignee: Darwin Discovery LimitedInventors: Robin Mark Bannister, Graham Evans
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Patent number: 5846999Abstract: The compounds of the formula: ##STR1## wherein R.sub.1 is straight chain alkyl, branched chain alkyl, cycloalkyl, hydroxyalkyl, fluoroalkyl or polyfluoroalkyl; R.sub.2 and R.sub.3 are, independently, hydrogen or an acyl substituent selected from the group consisting of formyl, alkanoyl, alkenoyl, alkoxycarbonyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; or a pharmaceutically acceptable salt thereof, relaxes smooth muscles.Type: GrantFiled: July 7, 1997Date of Patent: December 8, 1998Assignee: American Home Products CorporationInventors: Madelene M. Antane, Bradford H. Hirth, Russell F. Graceffa, John A. Butera
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Patent number: 5834618Abstract: 3-Amino-2-hydroxy-4-phenylbutyronitrile derivatives represented by the formula (3) may be prepared by reacting an aminoaldehyde derivative represented by the formula (1) with a cyanohydrin derivative represented by the formula (2) in the presence of a metallic compound, base, or acid; ##STR1## wherein R.sup.1 and R.sup.2 each independently represents a hydrogen atom or a protective group for an amino group, R.sup.3 and R.sup.4 each represents an alkyl or cycloalkyl group or R.sup.3 and R.sup.4 together form a tetramethylene or pentamethylene group.Type: GrantFiled: December 19, 1997Date of Patent: November 10, 1998Assignees: Kuraray Co., Ltd., Sagami Chemical Research CenterInventors: Shiro Terashima, Norio Shibata, Etsuko Itoh
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Patent number: 5763639Abstract: A process for preparing quaternized glycine nitriles of formula I ##STR1## comprising reaction of the corresponding precursor amine, aldehyde, hydrocyanic acid or alkali metal cyanide, and subsequent quaternization with an alkylating agent, wherein the reaction and quaternization are carried out successively in aqueous medium without isolation of an intermediate.Type: GrantFiled: March 3, 1997Date of Patent: June 9, 1998Assignee: BASF AktiengesellschaftInventors: Ulrich Annen, Hans-Peter Seelmann-Eggebert, Rudi Widder, Reinhard Muller
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Patent number: 5703266Abstract: The invention concerns the use of a 3-substituted para-aminophenol as an oxidation dye precursor for dyeing keratinous fibres, in particular human hair. The 3-substituted para-aminophenol has formula: ##STR1## where R.sub.1 represents alkyl, alkenyl, mono- or polyhydroxyalkyl, nitrile, cyanoalkyl, halogenoalkyl, aminoalkyl or alkoxyalkyl and R.sub.2 represents hydrogen, alkyl or mono- or polyhydroxyalkyl, provided that when R.sub.2 is hydrogen R.sub.1 is not methyl or trifluoromethyl, and to addition salts thereof with an acid. The invention also concerns dye compositions containing compound (I). The invention further concerns novel 3-substituted para-aminophenols.Type: GrantFiled: December 2, 1996Date of Patent: December 30, 1997Assignee: L'OrealInventors: Alain Lagrange, Jean Jacques Vandenbosche, Jean Cotteret, Marie Pascale Audousset
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Patent number: 5637770Abstract: A novel hexa-cyclic compound, a derivative of camptothecin, of the general formula: ##STR1## The compound is prepared from an aminoketone compound and a pyranoindolizine compound by the condensation-ring closing reaction. It is abundantly water-soluble, and has an excellent antitumour activity and a high degree of safety, and can be applied as an antitumour medicine for curing tumors of various kinds.Type: GrantFiled: May 31, 1995Date of Patent: June 10, 1997Assignees: Daiichi Pharmaceutical Co., Ltd., Kabushiki Kaisha Yakult HonshaInventors: Hirofumi Terasawa, Akio Ejima, Satoru Ohsuki, Kouichi Uoto
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Patent number: 5631405Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.Type: GrantFiled: June 7, 1995Date of Patent: May 20, 1997Assignee: Pharm-Eco Laboratories, IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard L. Gabriel
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Patent number: 5629442Abstract: A process is disclosed to produce an .alpha.-hydroxyiminophenylacetonitrile of the general formula [II]: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and Z are each as defined in the specification, characterized in that a crude nitrile containing a phenylacetonitrile of the general formula [I]: ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and Z are each as defined in the specification, is reacted with an alkyl nitrite in the presence of a base, after which the reaction mixture is extracted with water and then the separated aqueous layer is neutralized with an acid. According to this production process, the desired .alpha.-hydroxyiminophenylacetonitrile can be produced with high purity, in high yield and with ease by extracting the reaction mass with water and then neutralizing the separated aqueous layer with an acid.Type: GrantFiled: May 11, 1995Date of Patent: May 13, 1997Assignees: Shionogi & Co., Ltd., Sumitomo Chemical Company, Ltd.Inventors: Akira Takase, Hiroyuki Kai, Moriyasu Masui, Katuhisa Masumoto, Akihiko Nakamura, Yujiro Kiyoshima, Mikio Sasaki
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Patent number: 5618966Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.Type: GrantFiled: May 16, 1995Date of Patent: April 8, 1997Assignee: Pharm-Eco Laboratories, IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
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Patent number: 5599994Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.The method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.Type: GrantFiled: June 7, 1995Date of Patent: February 4, 1997Assignee: Pharm-Eco Laboratories, Inc.Inventors: Biman Pal, Siya Ram, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard L. Gabriel
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Patent number: 5571942Abstract: The present invention provides novel ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes and 3-aminochromanes which exhibit binding activity at the serotonin 1A receptor.Type: GrantFiled: August 22, 1995Date of Patent: November 5, 1996Assignee: Eli Lilly and CompanyInventors: Craig S. Hoechstetter, Diane L. Huser, John M. Schaus, Robert D. Titus
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Patent number: 5543573Abstract: The present invention relates to a hydrazinecarboxamide derivative of the general formula (I) shown below: ##STR1## wherein the substituents are as defined in the specification, which has a wide insecticidal spectrum at a low dosage, a process for producing said derivative, and utilization of said derivative as an insecticide.Type: GrantFiled: April 14, 1994Date of Patent: August 6, 1996Assignee: Nihon Nohyaku Co., Ltd.Inventors: Kazuhiro Takagi, Takashi Ohtani, Tateki Nishida, Hiroshi Hamaguchi, Tetsuyoshi Nishimatsu, Atsushi Kanaoka
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Patent number: 5530014Abstract: The cyclohexadiene derivatives are prepared by reaction of cyclohexanones with amines and subsequent dehydration. The compounds are suitable as active compounds in medicaments on account of their property of being selective modulators of calcium channel-dependent potassium channels.Type: GrantFiled: August 18, 1995Date of Patent: June 25, 1996Assignee: Bayer AktiengesellschaftInventors: Klaus Urbahns, Hans-Georg Heine, Bodo Junge, Rudolf Schohe-Loop, Hartmund Wollweber, Henning Sommermeyer, Thomas Glaser, Reilinde Wittka, Jean-Marie-Viktor De Vry
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Patent number: 5523454Abstract: Ortho-substituted phenylacetamides I ##STR1## (R.sup.1 =H, alkyl, cycloalkyl, alkenyl, alkynyl, phenylalkynyl, alkoxyalkyl, alkoxycarbonyl, phenyl, phenylalkyl, phenylalkenyl or phenoxyalkyl, 5- or 6-membered heterocycle with 1-3 hetero atoms to which a benzene rang or a 5- or 6-membered heterocycle can be fused; R.sup.2 and R.sup.3 =H, CN, halogen, alkyl, alkoxy; R.sub.4 and R.sup.5 =H, alkyl and R.sup.4 or R.sup.5 =alkoxy; Y=O, S, SO, SO.sub.2, N.dbd.N, O--CO, CO--O, CO--O--CH.sub.2, alkylene or haloalkylene, alkenylene, alkynylene, oxy- alkylene, thio-alkylene, alkyleneoxy, carbonylalkylene or alkylenecarbonyl, W=alkoxyimino, alkoxymethylene or alkylthiomethylene), excepting compounds where R.sup.1 is hydrogen, phenyl or 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropyl, R.sup.2 to R.sup.5 are each hydrogen, Y is carbonyloxymethylene and W is methoxymethylene or methylthiomethylene, are suitable as fungicides and for controlling pests.Type: GrantFiled: May 12, 1995Date of Patent: June 4, 1996Assignee: BASF AktiengesellschaftInventors: Siegbert Brand, Eberhard Ammermann, Gisela Lorenz, Hubert Sauter, Klaus Oberdorf, Uwe Kardorff, Christoph Kuenast
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Patent number: 5498745Abstract: Novel compounds which are 2,6-di-t-butylphenols substituted on the 4 position by an anilino group, which anilino group is substituted by a carboxyl substituent, a tetrazolyl substituent or an N-methyltetrazolyl substituent, are useful antiallergic agents. Pharmaceutical compositions containing and pharmacological methods of using such compounds are also disclosed, as are synthetic intermediates for preparing such compounds. Certain of the synthetic intermediates also exhibit useful antiallergic activity.Type: GrantFiled: May 5, 1995Date of Patent: March 12, 1996Assignee: Riker Laboratories, Inc.Inventor: Robert A. Scherrer
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Patent number: 5498746Abstract: Process for the preparation of 5,6-dihydroxyindole, wherein the compound of formula: ##STR1## in which R' denotes a hydrogen atom or an optionally substituted benzyl radical, is subjected either to the action of hydrogen under pressure or to a hydrogen transfer operation, in a solvent medium and in the presence of a hydrogenation catalyst.Type: GrantFiled: June 5, 1995Date of Patent: March 12, 1996Assignee: L'OrealInventors: Alex Junino, Jean J. Vandenbossche, Gerard Lang
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Patent number: 5492641Abstract: .beta.-Aminonitriles of the following formula I ##STR1## where R.sup.1 is an aliphatic hydrocarbon radical having alkyl side groups and a number average molecular weight of from 250 to 5,000 and R.sup.2, R.sup.3 and R.sup.4, independently of one another, are each hydrogen or C.sub.1 -C.sub.8 -alkyl and R.sup.2 or R.sup.4 is also phenyl, and alkylpropylenediamines prepared from the .beta.-aminonitriles by hydrogenation are used as additives in fuels and lubricants.Type: GrantFiled: November 21, 1994Date of Patent: February 20, 1996Assignee: BASF AktiengesellschaftInventors: Juergen Mohr, Knut Oppenlaender, Lothar Franz, Juergen Thomas
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Patent number: 5476960Abstract: An .alpha.-aminonitrile compound derived from the reaction, in the presence of a cyanide source of (1) a bisulfite adduct of a carbonyl compound selected from the group consisting of an aldehyde and a ketone with (2) a fatty alkyl alkylene diamine containing two reactible amino functionalities which is of the formula RNHR.sub.1 NH.sub.2, where R is fatty alkyl and R.sub.1 is lower alkylene of up to six carbon atoms.Type: GrantFiled: April 7, 1994Date of Patent: December 19, 1995Assignee: Akzo Nobel N.V.Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
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Patent number: 5475138Abstract: The present invention relates to a method of forming a 1,3-diamino-3-substituted-2-propanol chemical intermediate from which various chemicals, such as selected protease-inhibitors and other drugs, as well as polymers, can be synthesized.This method includes contacting a nitromethyl amino acid compound with at least one reducing agent to form the 1,3-diamino-3-substituted-2-propanol chemical intermediate.Type: GrantFiled: July 7, 1994Date of Patent: December 12, 1995Assignee: Pharm-Eco Laboratories IncorporatedInventors: Biman Pal, Siya Ram, Bing Cai, Yesh P. Sachdeva, Jaechul Shim, Salah A. Zahr, Emile Al-Farhan, Richard Gabriel
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Patent number: 5457131Abstract: The present invention relates to cyclopentane heptanoic or cyclopentane heptenoic acid, 2-hydrocarbyl sulfonamidomethyl, and derivatives thereof, useful as therapeutic agents. In particular, the therapeutic agents of this invention are useful as ocular hypotensives.Type: GrantFiled: August 18, 1994Date of Patent: October 10, 1995Assignee: Allergan, Inc.Inventor: Steven W. Andrews
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Patent number: 5451607Abstract: There are disclosed hydrazone derivatives of the general formula [I]: ##STR1## wherein R.sup.1 is halogen, etc.; R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl, etc.; R.sup.3 is hydrogen or C.sub.1 -C.sub.6 alkyl, etc.; R.sup.4 is hydrogen or C.sub.1 -C.sub.6 alkyl, etc.; R.sup.5 is C.sub.1 -C.sub.6 alkyl, etc.; R.sup.6 is hydrogen or C.sub.1 -C.sub.6 alkyl, etc.; A is (CH.sub.2).sub.t, O, S(O).sub.n, etc.; a is an integer of 1 to 4; n is an integer of 0 to 2; and t is an integer of 1 to 3; as well as production processes therefor, insecticides and/or acaricides containing the same as an active ingredient and intermediate compounds thereof.Type: GrantFiled: April 19, 1993Date of Patent: September 19, 1995Assignee: Sumitomo Chemical Co., Ltd.Inventors: Toshiaki Taki, Hirosi Kisida, Shigeru Saito, Shinji Isayama
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Patent number: 5416111Abstract: Non-peptidyl compounds characterized generally as .alpha.-succinamidoacyl aminodiols containing a cyano group and having an N-phenyl-amino-type group at the N-terminus are useful as renin inhibitors for the treatment of hypertension.Type: GrantFiled: December 16, 1993Date of Patent: May 16, 1995Assignee: G.D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran
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Patent number: 5410067Abstract: Process for the preparation of 5,6-dihydroxyindole, wherein the compound of formula: ##STR1## in which R' denotes a hydrogen atom or an optionally substituted benzyl radical, is subjected either to the action of hydrogen under pressure or to a hydrogen transfer operation, in a solvent medium and in the presence of a hydrogenation catalyst.Type: GrantFiled: July 29, 1992Date of Patent: April 25, 1995Assignee: L'OrealInventors: Alex Junino, Jean J. Vandenbossche, Gerard Lang
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Patent number: 5407961Abstract: The present invention is concerned with antiretroviral (e.g. anti HIV-1) compounds having the formula ##STR1## Pharmaceutical compositions containing said compounds of formula (I-a) or (I-b), and processes of preparing said compounds and compositions.Type: GrantFiled: May 12, 1994Date of Patent: April 18, 1995Assignee: Janssen Pharmaceutica N.V.Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Frans M. A. Van den Keybus, Karin J. M. M. Nuyens, Paul A. J. Janssen
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Patent number: 5391808Abstract: N,N,N',N'-Tetrasubstituted 1,4-diamino-2-butenes where the substituents are alkyl, cycloalkyl, aralkyl, aryl or mixtures thereof provide effective antioxidant protection to lubricants and/or synthetic polymers.Type: GrantFiled: November 1, 1993Date of Patent: February 21, 1995Assignee: Ciba-Geigy CorporationInventors: Joseph E. Babiarz, Glen T. Cunkle, Werner Rutsch
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Patent number: 5387608Abstract: The present invention relates to cyclopentane heptanoic or cyclopentane heptenoic acid, 2-hydrocarbyl sulfonamidomethyl, and derivatives thereof, useful as therapeutic agents. In particular, the therapeutic agents of this invention are useful as ocular hypotensives.Type: GrantFiled: August 17, 1993Date of Patent: February 7, 1995Assignee: Allergan, Inc.Inventor: Steven W. Andrews
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Patent number: 5374763Abstract: .alpha.-aminonitrile compounds derived from a fatty alkyl alkylene diamine containing two reactible amino functionalities are disclosed which are of the formula ##STR1## where R is C.sub.12 -C.sub.22 fatty alkyl, R.sub.1 is alkylene, R.sub.2 is alkyl, and R.sub.3 is alkyl or hydrogen.Type: GrantFiled: April 6, 1994Date of Patent: December 20, 1994Assignee: Akzo Nobel n.v.Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
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Patent number: 5374762Abstract: .alpha.-aminonitrile compounds derived from a fatty alkyl alkylene diamine containing two reactible amino functionalities are disclosed which are of the formula ##STR1## where R is C.sub.12 -C.sub.22 fatty alkyl, R.sub.1 is alkylene, R.sub.2 is aryl, and R.sub.3 is alkyl, aryl, or hydrogen.Type: GrantFiled: April 6, 1994Date of Patent: December 20, 1994Assignee: Akzo Nobel N.V.Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
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Patent number: 5371265Abstract: .alpha.-aminonitrile compounds derived from a fatty alkyl alkylene diamine containing two reactible amino functionalities are disclosed which are of the formula ##STR1## where R is C.sub.12 -C.sub.22 fatty alkyl, R.sub.1 is alkylene, R.sub.2 is aryl, and R.sub.3 is aryl or hydrogen.Type: GrantFiled: April 7, 1994Date of Patent: December 6, 1994Assignee: Akzo Nobel N.V.Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
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Patent number: 5334745Abstract: 3-Aminopropionitriles of the general formula I ##STR1## where R.sup.1,R.sup.2,R.sup.3,R.sup.4 and R.sup.5 independently of one another are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.8 -aminoalkyl, C.sub.1 -C.sub.8 -cyanoalkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.7 -C.sub.20 -aralkyl or aryl,are prepared by a process in which an amine of the general formula II ##STR2## is reacted with an acrylonitrile of the general formula III ##STR3## where the substituents have the abovementioned meanings, in a molar ratio of from 0.9:1 to 100:1 over a heterogeneous catalyst at from 40.degree. to 200.degree. C. and from 1 to 350 bar.Type: GrantFiled: May 28, 1993Date of Patent: August 2, 1994Assignee: BASF AktiengesellschaftInventors: Martin Brudermueller, Tom Witzel, Franz Merger
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Patent number: 5332826Abstract: This invention relates to a process for preparing aminoacetonitriles in one vessel. The process involves the steps of: (A) reacting an alkali metal cyanide with an aldehyde in water to form a cyanohydrin; (B) extracting the cyanohydrin formed in Step (A) into a water immiscible solvent to form a two phase system comprising a water immiscible phase containing the cyanohydrin and an aqueous phase; (C) removing at least 50 weight percent, based on the weight of the water immiscible phase, of the water immiscible solvent from the water immiscible phase thereby concentrating the cyanohydrin; (D) adding a water miscible amide solvent to the concentrated cyanohydrin to form a cyanohydrin solution; and (E) passing ammonia through the cyanohydrin solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.Type: GrantFiled: October 13, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventor: Paul R. Buckland
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Patent number: 5332825Abstract: This invention relates to two processes for preparing aminoacetonitriles in one vessel under anhydrous conditions. Process I involves the steps of: (A) reacting trimethylsilyl cyanide and an aldehyde in a water miscible amide solvent to obtain a silyl blocked cyanohydrin solution; (B) adding a catalytic amount of water to the silyl blocked cyanohydrin solution from Step (A); and (C) passing ammonia through the solution to obtain an aminoacetonitrile. Process II involves the steps of: (A') reacting trimethylsilyl cyanide with an aldehyde in the absence of solvent to form a silyl blocked cyanohydrin; (B') adding a water miscible amide solvent to the silyl blocked cyanohydrin from Step (A') to obtain a solution; and (C') passing ammonia through the solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.Type: GrantFiled: October 13, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventor: Paul R. Buckland
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Patent number: 5319126Abstract: .alpha.-aminonitrile compounds derived from a fatty alkyl alkylene diamine containing two reactible amino functionalities are disclosed.Type: GrantFiled: January 29, 1993Date of Patent: June 7, 1994Assignee: Akzo n.v.Inventors: Alison A. Fleming, Robert F. Farmer, James F. Gadberry
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Patent number: 5294730Abstract: Antidepressant agents having the formula ##STR1## wherein R.sup.1 is a polycycloalkyl group; R.sup.2 is methyl or ethyl, X is O or NH; and Y comprises a 5- or 6-membered heterocyclic ring having one or two nitrogens; or fused bicyclic heterocyclic rings having a total of three nitrogen atoms, one in each ring and one angular nitrogen.Type: GrantFiled: November 20, 1992Date of Patent: March 15, 1994Assignee: Pfizer Inc.Inventors: Nicholas A. Saccomano, Fredric J. Vinick
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Patent number: 5290806Abstract: 4-4(tert-butylphenyl)-cyclohexylamines and quaternary ammonium salts thereof of the formulae ##STR1## where R.sup.1 is hydrogen, alkyl or alkenyl,R.sup.2 is alkyl, haloalkyl, hydroxyalkyl, cycloalkyl, alkylcycloalkyl, bicycloalkyl, alkenyl, unsubstituted or mon- to trisubstituted phenyl, or unsubstituted or mono- to trisubstituted phenylalkyl,X.crclbar. is a plant-tolerated acid anion,and their plant-tolerated acid addition salts, and fungicides containing these compounds.Type: GrantFiled: July 2, 1993Date of Patent: March 1, 1994Assignee: BASF AktiengesellschaftInventors: Bernhard Zipperer, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5247119Abstract: A class of substituted phenylacetonitrilehydroxyalkylaminoalkyl-ortho-substituted aryl compounds having immunosuppressive properties is described. Compounds of this class would be useful in reducing recipient rejection of transplanted organs and for treatment of autoimmune or inflammatory diseases. Compounds of particular interest are of the formula ##STR1## wherein each of m and n is a number independently selected from one to five, inclusive; wherein R.sup.1 is selected from hydrido, alkyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkenyl and alkynyl; wherein R.sup.6 is selected from loweralkyl; wherein each of R.sup.8, R.sup.9, R.sup.10 and R.sup.12 through R.sup.16 is independently selected from hydrido, hydroxy, alkyl, hydroxyalkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonylalkenyl, alkylaminocarbonyl and alkoxyalkyl; or a tautomer thereof or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: May 28, 1992Date of Patent: September 21, 1993Assignee: G. D. Searle & Co.Inventors: Kerry W. Fowler, John M. Farah, Jr., John P. McKearn, Richard A. Mueller, Susan A. Gregory
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Patent number: 5223536Abstract: The 1,4-diaryl-1-cyclopropyl-4-substituted butane pesticides of the following formula are effective as insecticides and acaricides: ##STR1## in which X and Y are independently hydrogen, halogen, alkyl, alkoxy, cycloalkylalkoxy, alkylcarbonyl, alkoxycarbonyl, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, trialkylamino, nitro, or cyano; or X and Y together are --OCH.sub.2 O-- or --OCF.sub.2 O-- bridging the 2-3 or 3-4 positions of the phenyl ring; Ar is 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, 6-phenoxypyridin-2-yl, or 2-methyl(1,1'-biphenyl)-3-yl;R is cyano, methyl, trifluoromethyl, alkenyl, alkynyl, or halogen.Type: GrantFiled: July 23, 1991Date of Patent: June 29, 1993Assignee: FMC CorporationInventors: Thomas G. Cullen, Scott McN. Sieburth, Gary A. Meier, John F. Engel
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Patent number: 5196562Abstract: Protecting against parasitic protozoa with substituted 1,3,5-triazinetriones of the formula ##STR1## in which R.sup.1 represents aromatic or heteroaromatic radicals, each of which is optionally substituted,R.sup.2 represents H, alkyl, alkenyl, alkinyl or aralkyl, each of which is optionally substituted,R.sup.3 represents one or more identical or different radicals from the group consisting of hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, alkylthio, halogenoalkoxy, halogenoalkylthio, cyano, alkoxycarbonyl, alkylsulphonyl and halogenoalkylsulphonyl,R.sup.4 represents hydrogen, a straight-chain, branched or cyclic alkyl radical, alkenyl, alkinyl, aralkyl or aryl, each of which is optionally substituted, andR.sup.5 represents hydrogen, optionally substituted alkyl, alkenyl, alkinyl or aralkyl.Also novel intermediates therefor.Type: GrantFiled: December 27, 1989Date of Patent: March 23, 1993Assignee: Bayer AktiengesellschaftInventors: Werner Lindner, Axel Haberkorn
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Patent number: 5196147Abstract: An organic nonlinear optical substance having the formula (I): ##STR1## wherein R.sup.1 represents --H or --CH.sub.3 ;n is 0, 1, or 2;A represents Z.sup.1 --Ar, ##STR2## wherein Ar represents a 6-14 membered aromatic group including a heterocyclic ring or bisphenylene type ring; Z.sup.1 represents H--, R.sup.5 R.sup.6 N--, R.sup.7 O--, R.sup.8 S--, NC--, R.sup.9 OCO--, R.sup.10 COO--, O.sub.2 N--, R.sup.11 R.sup.12 NOC, R.sup.13 CO(R.sup.14)N--, or R.sup.15 --; Z.sup.2, Z.sup.3, and Z.sup.4 independently represent H--, a C.sub.1 -C.sub.8 alkyl--, R.sup.16 O--, R.sup.17 R.sup.18 N, R.sup.19 S--, O.sub.2 N--, or two R.sup.16 being, in combination, R.sup.20 CH<; R.sup.2 represents H-- or a C.sub.1 -C.sub.12 alkyl; R.sup.5 to R.sup.20 independently represent H--, or a C.sub.1 -C.sub.10 hydrocarbon residue; Z.sup.5 independently represents H--, a C.sub.1 -C.sub.8 saturated hydrocarbon residue, O.sub.2 N--, R.sup.21 O--, R.sup.22 S--, NC--, or R.sup.23 R.sup.24 N-- wherein R.sup.21 to R.sup.Type: GrantFiled: March 28, 1989Date of Patent: March 23, 1993Assignee: Teijin LimitedInventors: Yutaka Taketani, Hiroshi Matsuzawa, Kaoru Iwata
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Patent number: 5180744Abstract: Non-peptidyl compounds characterized generally as aralkyl-N-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from ##STR2## wherein each of Y and Z is independently selected from hydrido, chloro, fluoro, methoxy and dimethylamino; wherein n is a number selected from zero through four, inclusive; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; wherein R.sub.7 is isobutyl or ethyl; and wherein each of R.sub.8 and R.sub.9 is hydrido; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: July 29, 1991Date of Patent: January 19, 1993Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
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Patent number: 5169865Abstract: A method, and mediating agents are provided for mediating the physiological effects of hormones, neurotransmitters, calcium-channel antagonists, chemotactic peptides or chemotactic proteins. The mediating agents provided herein are bioactive conformations of peptide hormones, neurotransmitters, calcium-channel antagonist drugs or chemotatic peptides, or analogues, agonists or antagonists thereof, or synthetic analogue substances, having Ca.sup.2+ and/or Mg.sup.2+ ions optimally and optimally-conformationally bound to the respective compound. The Ca.sup.2+ antagonist/agonist may bind Mg.sup.2+ and thus may also block calcium-channel. In the one method, the concentration of intracellular Ca.sup.2+ is raised by means of such mediating agents. A second method is also provided for delivering Ca.sup.2+ and/or Mg.sup.2+ to a membrane-bound receptor by transporting Ca.sup.2+ and/or Mg.sup.2+ through a cell membrane using the above-described mediating agents.Type: GrantFiled: March 14, 1989Date of Patent: December 8, 1992Assignee: Seabright Corporation LimitedInventor: V. S. Ananthanarayanan
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Patent number: 5169973Abstract: Alpha-aminonitriles can be synthesized by the reaction, at ambient temperature without use of catalyst, of essentially stoichiometric amounts of amine, aldehyde (either monoaldehyde or dialdehyde) and trimethylsilyl cyanide.Type: GrantFiled: April 15, 1991Date of Patent: December 8, 1992Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Harry W. Gibson, Jean-Pierre LeBlanc
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Patent number: 5167696Abstract: A compound of formula (I): ##STR1## in which Ar is an optionally substituted aryl or heterocyclic ring system; W is O or NR.sup.1 where R.sup.1 is hydrogen or lower alkyl;A is .dbd.CH or >CH.sub.2 and G is .dbd.C--R.sup.2, >CR.sup.3 R.sup.4 or >C.dbd.R.sup.5 such that --G--A-- is --CR.sup.2 .dbd.CH--, where R.sup.2 is H or CR.sup.6 R.sup.7 XR.sup.8 ; or --G--A-- is CR.sup.3 R.sup.4 --CH.sub.2 where CR.sup.3 R.sup.4 is CH--CR.sup.6 R.sup.7 XR.sup.8, CH--OCR.sup.6 R.sup.7 XR.sup.8, C(R.sup.9)OCOR.sup.10, CR.sup.9 R.sup.10, C(R.sup.9)OR.sup.10, C(OR.sup.9)OR.sup.10, or CH--CH.sub.2 (CO.sub.2 R.sup.11); or --G--A-- is --CR.sup.5 --CH.sub.2 -- where R.sup.5 is .dbd.CR.sup.7 XR.sup.8, .dbd.NOCR.sup.6 R.sup.7 XR.sup.8, .dbd.NOR.sup.11 or .dbd.NOCOR.sup.11 ;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.20)CH.sub.2, or COCH.sub.2 ;n is 0, 1 or 2;R.sup.6 and R.sup.7 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.9 R.sup.10, or R.sup.6 and R.sup.Type: GrantFiled: February 7, 1991Date of Patent: December 1, 1992Assignee: Imperial Chemical Industries PLCInventors: Ewan J. T. Chrystal, John E. D. Barton, David Cartwright
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Patent number: 5166347Abstract: Novel carboximidamide derivatives represented by the following formula (A) and acid adduct salts thereof are disclosed: ##STR1## wherein all the substituents have the same meanings as defined above. N-cyano-pyridinecarboximidate compounds represented by the following formula (II) which are the intermediates for preparing of N-cyano-N'-substituted-pyridinecarboximidamide derivatives wherein the substituent B in the above described formula (A) is pyridine is also disclosed: ##STR2## wherein all the substitutents have the same meanings as defined above. The process for preparing the compounds, the pharmaceutical agents comprising the compound having vasodilating effect, and the therapeutic method of dosing the compound on patients for therapy are also disclosed.Type: GrantFiled: December 22, 1989Date of Patent: November 24, 1992Assignee: Kirin Beer Kabushiki KaishaInventors: Toshio Izawa, Tomoko Kashiwabara, Shohachi Nakajima, Nobuyuki Ogawa