Chalcogen Attached Indirectly To The Piperidine Ring By Nonionic Bonding Patents (Class 546/248)
  • Patent number: 5051511
    Abstract: Compounds which contain peroxide linkages as well as a hindered amine light stabilizer moiety of low basicity function as free radical polymerization initiators and provide a polymer containing a hindered amine stabilizer chemically bonded to said polymer. The low basicity of the instant compounds prevents interaction with acid catalysts used in some polymerization systems.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: September 24, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Roland A. E. Winter, Peter J. Schirmann
  • Patent number: 5041545
    Abstract: Hydrazide functionalized 2-hydroxybenzophenone ultraviolet light and heat stabilizers and derivatives are disclosed having the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X, Y, Z, all substituents thereof, and n are set forth in the Summary of the Invention. Y--N(R.sup.6)--Z is the hydrazide or derivative group and --X--R.sup.5 -- links the hydrazide group to an aromatic nucleus of the optionally substituted benzophenone group. Derivatives are, for example, acyl hydrazides, diacyl hydrazides (including imides), hydrazones and alkyl hydrazides. The compounds are useful as ultraviolet light absorbers and heat stabilizers for plastics.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: August 20, 1991
    Assignee: Atochem North America, Inc.
    Inventor: Terry N. Myers
  • Patent number: 5037978
    Abstract: An ester of a carboxylic acid is prepared via a transesterification reaction which comprises reacting a lower alkyl ester of carboxylic acid with a higher alkyl alcohol in the presence of a catalyst consisting of a hafnium chelate derived from hafnium tetrachloride, bis(alkoxide)hafnium dichlorides, or hafnium tetraalkoxides in the presence of 1,3-dicarbonyl compounds.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: August 6, 1991
    Assignee: Rohm and Haas Company
    Inventor: Mario G. L. Mirabelli
  • Patent number: 5017693
    Abstract: The present invention provides cleavable conjugates whose linkers contain a labile bond that is cleavable under a variety of mild conditions, including weakly acidic. Since the agent may be bonded directly to the linker, cleavage can result in release of native agent. The invention also provides methods for producing cleavable conjugates. Preferred agents include drugs, toxins, biological response modifiers, radiodiagnostic compounds, radiotherapeutic compounds, and derivatives thereof. The targeting molecule employed in the invention may be an intact molecule, a fragment thereof, or a functional equivalent thereof. In a particularly preferred embodiment, the targeting molecule is a monoclonal antibody directed towards a tumor-associated antigen in man. The invention further provides methods for delivering to the cytoplasm of target cell an agent free of its targeting molecular carrier.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: May 21, 1991
    Assignee: NeoRx Corporation
    Inventors: Mark D. Hylarides, Ananthachari Srinivasan, Jeffrey N. Fitzner, Vivekananda M. Vrudhula
  • Patent number: 5010189
    Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonization of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.
    Type: Grant
    Filed: October 24, 1989
    Date of Patent: April 23, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 5010200
    Abstract: This invention provides novel insecticidally and acaricidally active pyrimidine derivatives of formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is selected from alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; and cycloalkyl optionally substituted by alkyl or halogen;R.sup.2 is selected from alkyl; haloalkyl; alkoxy; alkylamino; dialkylamino; halogen; cycloalkyl optionally substituted by halogen or alkyl; and phenyl optionally substituted by alkyl, haloalkyl, halogen or alkoxy;R.sup.3 is selected from hydrogen and halogen;R.sup.4 is the residue of an alcohol of formula R.sup.4 -OH which forms an insecticidal ester when combined with chrysanthemic acid, permethrin acid or cyhalothrin acid; andX is selected from oxygen and sulphur.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: April 23, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Edward McDonald, Roger Salmon, Alan J. Whittle, Michael G. Hutchings
  • Patent number: 5001156
    Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 [OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: March 19, 1991
    Assignee: L'Oreal
    Inventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
  • Patent number: 4992150
    Abstract: A process for preparing oil-soluble nitrogen-containing compounds which comprises subjecting nitrogen-containing telogens and alpha-olefin taxogens to radical telomerization reaction. The nitrogen-containing compounds are mixtures of telomers having an average molecular weight not less than 300 and a nitrogen content of from 0.1 to 10 wt %. The compound may be further reacted with boron-bearing compounds or boron compounds to obtain oil-soluble nitrogen and boron-containing compounds. These compounds are useful as additives for fuel oils and lubricating oils.
    Type: Grant
    Filed: April 13, 1989
    Date of Patent: February 12, 1991
    Assignee: Nippon Oil Co, Ltd.
    Inventors: Jinichi Igarashi, Harumichi Watanabe
  • Patent number: 4985556
    Abstract: Perfluorocarboxylic acid fluorides represented by the formula A-B, wherein A is either ##STR1## and B stands for a perfluoro-di-substituted amino group, and perfluoro(dialkylaminopropenes) represented by the formula A"-B", wherein A" stands for ##STR2## and B" has the same meaning as B defined above, are novel compounds. Methods for the production of these novel compounds are also disclosed.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: January 15, 1991
    Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventors: Takashi Abe, Eiji Hayashi
  • Patent number: 4980378
    Abstract: Biodegradable absorption enhancers, especially useful in pharmaceutical formulations, are compounds having the formula ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.7 alkyl, benzyl or 4-hydroxybenzyl; n is a whole number from 4 to 18 inclusive; R.sub.1 and R.sub.2 are independently selected from hydrogen and C.sub.1 -C.sub.7 alkyl, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached are combined to form a substituted or unsubstituted heterocycloalkyl radical having a total of 5 to 7 ring atoms, optionally including a hetero ring atom selected from oxygen, sulfur and nitrogen in addition to the indicated nitrogen atom, the substituents when present being one to three C.sub.1 -C.sub.7 alkyl radicals, which may be the same or different; and R.sub.3 and R.sub.4 are independently selected from hydrogen, methyl and ethyl.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: December 25, 1990
    Assignee: Odontex, Inc.
    Inventors: Ooi Wong, Toshiaki Nishiahta, Joseph H. Rytting
  • Patent number: 4971979
    Abstract: Substituted alkadienes of formula: ##STR1## in which R.sub.1 is hydroxy or acetoxy, R.sub.2 is hydrogen, carboxy, alkoxycarbonyl, phenyl or benzoyl, andR.sub.3 is alkylthio or alkoxy and R.sub.4 is naphthoyl or optionally substituted benzoyl,or R.sub.3 is alkoxycarbonyl, cycloalkyloxycarbonyl or cyano and R.sub.4 is alkyl, naphthyl, optionally substituted phenyl, alkylthio, naphthylmethanethio, optionally substituted benzylthio, optionally substituted phenylthio, naphthylthio, phenethylthio or allylthio,or R.sub.3 and R.sub.4 form, with the carbon atom to which they are attached, a ring-system of formula: ##STR2## in which R.sub.5 is hydrogen or alkoxy and X is methylene or S inhibit 5-lipoxygenase and are useful, for example, as anti-inflammatories.
    Type: Grant
    Filed: July 19, 1989
    Date of Patent: November 20, 1990
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Luc Malleron, Gerard Ponsinet, Gerard Roussel
  • Patent number: 4960774
    Abstract: Amines of the general formula I ##STR1## where n is an integer from 2 to 10, X is oxygen or sulfur, Z is oxygen or CH--R.sub.5, and R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are each hydrogen or alkyl, salts thereof, and fungicides containing these compounds.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 4940707
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are lower-alkyl; or together are alkylene with 3-5 C-atoms in a straight chain; one of the residues R.sup.3 and R.sup.4 is hydrogen and the other is hydrogen or lower-alkyl; R.sup.6 and R.sup.7 are hydrogen or lower-alkyl; R.sup.5 and R.sup.8 are hydrogen, lower-alkyl, lower-alkoxy or halogen; X signifies --O--, --S--, --SO--, --SO.sub.2 -- or --NR.sup.9 ; R.sup.9 is hydrogen, lower-alkyl or acyl; Y is --S(O).sub.m R.sup.10 or --NHet and, where X is --NR.sup.9 --, --S--, --SO-- or --SO.sub.2 --, also --N(R.sup.11).sub.2 or --OR.sup.12 ; R.sup.10 is lower-alkyl; R.sup.11 and R.sup.12 are hydrogen, lower-alkyl or acyl; --NHet is a 5-8 membered, saturated or unsaturated, monocyclic heterocycle, attached via a N-atom; n is 2, 3 or 4 and m is 0, 1 or 2, are described. The compounds of formula I are useful as agents for the treatment of disorders such as neoplasms, dermatoses or ageing of the skin.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: July 10, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
  • Patent number: 4920232
    Abstract: Known and novel substituted acroleins of the general formula I ##STR1## where R.sup.1 is alkoxy, phenoxy, halogen, haloalkyl, haloalkoxy, haloalkylthiyl or nitro, n is an integer from 1 to 5, in the case of n being greater than 1 the R.sup.1 s being identical or different and in the event of nitro substitution the aromatic ring carrying not more than 3 nitro groups, and where R.sup.2 is alkyl, cycloalkyl, unsubstituted or substituted aryl or hetaryl or a nonaromatic heterocyclic radical, are prepared by reacting a phenylacetaldehyde of the general formula II ##STR2## with an aldehyde of the general formula III[R.sup.2 -CHO] IIIin the presence of a base and a solvent. These acroleins are useful to prepare hydroxymethyloxiranes which are intermediates in the synthesis of antimycotic and fungicidal azoylmethyloxiranes.
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: April 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Goetz, Stefan Karbach, Hans-Gert Recker
  • Patent number: 4916162
    Abstract: Novel 3-hydroxy-3-methylglutary-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1## and pharmaceutically acceptable salts of the compounds (II) in which Z is hydrogen are disclosed.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: April 10, 1990
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Clarence S. Rooney, Ta Jyh Lee
  • Patent number: 4910304
    Abstract: N-substituted cyclic amines of the general formula I ##STR1## where A is an alkylene group or a --(CH.sub.2).sub.n --[--O--(CH.sub.2).sub.m ].sub.r group which may be monosubstituted or polysubstituted by radicals R without the radicals R in a defined compound having to be identical, R is alkyl, alkoxyalkyl, unsubstituted or alkyl-substituted or alkoxy-substituted cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, n and m independently of one another are each from 2 to 8 and r is from 1 to 3, the --(CH.sub.2).sub.n --[O--(CH.sub.2).sub.m ].sub.r group consisting of from 5 to 12 members, are prepared by reacting a primary amine of the general formula IIR--NH.sub.
    Type: Grant
    Filed: March 31, 1989
    Date of Patent: March 20, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Roman Fischer, Herbert Mueller, Dieter Voges
  • Patent number: 4910331
    Abstract: This invention relates to a process for producing a thiolsulfonic acid derivative of the general formula: ##STR1## wherein each of R.sub.1 and R.sub.2 is independently a lower alkyl group or a 5- or 6-membered cycloalkyl group, or alternatively R.sub.1 and R.sub.2 together with the adjacent nitrogen atom form a 5- or 6-membered heterocyclic group which may further contain an oxygen, sulfur or nitrogen atom; and R.sub.3 is (1) an aryl group which may optionally be substituted by a lower alkyl group, a halogen, a lower alkoxy group or a lower alkylthio group, (2) a lower alkyl group which may optionally be substituted by a lower alkoxy group, (3) an aralkyl group or (4) a cycloalkyl group, or a salt thereof, which comprises reacting a compound of the general formula: ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, or a salt thereof with a compound of the general formula:R.sub.3 SO.sub.2 H (II)wherein R.sub.3 is as defined above, or a salt thereof under an acid condition.
    Type: Grant
    Filed: October 7, 1988
    Date of Patent: March 20, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kazuaki Kihara, Makoto Kuroda, Toshiyuki Nakamura
  • Patent number: 4904788
    Abstract: Hydrocarbon-soluble complexes of magnesium alkoxides with magnesium amides are described. The magnesium amide moiety is derived from an amine (e.g., an N-heterocyclic amine). The complexes can be formed by reaction between a magnesium alkyl and a mixture of aliphatic alcohols and an amine.
    Type: Grant
    Filed: June 7, 1988
    Date of Patent: February 27, 1990
    Assignee: Texas Alkyls, Inc.
    Inventors: Andrzej M. Piotrowski, Dennis B. Malpass
  • Patent number: 4902818
    Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## in which R.sup.2 and R.sup.3 represents lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring, by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen, is described.The compounds of formula I are potential intermediates in the manufacture of, interalia, natural vitamin E and natural vitamin K.sub.1.
    Type: Grant
    Filed: October 5, 1988
    Date of Patent: February 20, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
  • Patent number: 4889953
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: December 26, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
  • Patent number: 4889656
    Abstract: Perfluoro(cycloaliphatic methyleneoxyalkylene) compositions are provided. These compositions comprise perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds having (a) a perfluorocycloaliphatic moiety which can have up to two perfluoroalkyl substituents and a perfluoroalkylene substituent, and (b) a perfluoromethyleneoxyalkylene carbonyl fluoride radical, the methylene group of the radical being bonded to a ring carbon atom or the perfluoroalkylene substituent of the moiety and the alkylene group of the perfluoromethyleneoxyalkylene carbonyl fluoride being a perfluoro(methyl)methylene group, a perfluoroisopropyleneoxy(methyl)methylene group, or a poly(perfluoroisopropyleneoxy)perfluoro(methyl)methylene group having up to about 10 perfluoroisopropyleneoxy units.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: December 26, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Richard M. Flynn, Patricia M. Savu
  • Patent number: 4882326
    Abstract: Piperidine compounds of the formula: ##STR1## or isomers thereof as well as pharmaceutically acceptable salts and/or hydrate forms thereof, and piperidine compounds of the formula: ##STR2## or isomers thereof as well as salt and/or hydrate forms thereof. In the above formulae, A represents a methylene group, an oxygen atom or a sulfur atom; B represents an oxygen atom or a sulfur atom; R.sup.1 and R.sup.2 independently represent a hydrogen atom, a lower alkyl group or an aralkyl group; R.sup.3 represents a hydrogen atom or an amino protecting group; Z represents an amino group or a protected amino group, a hydroxy group, or a reactive atom or group; m represents 1 or 2; and n represents the integer of 0 to 3.Piperidine compounds (I) possess an inhibitory activity against angiotensin-converting enzyme, and exhibit a long lasting hypotensive activity and are useful as antihypertensive agents. Piperidine compounds (II) are useful as intermediates for said piperidine compounds (I).
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: November 21, 1989
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Shu Murakami, Tsuguo Ikebe, Ichiro Hakamada, Osamu Yaoka
  • Patent number: 4861890
    Abstract: A process for producing chiral enamines by isomerizing a beta, gamma unsaturated amine with a rhodium-diphosphine complex with the addition of an achiral triarylphosphine and, if desired, hydrolyzing the compound of the enamine I obtained to the corresponding aldehyde.
    Type: Grant
    Filed: August 10, 1987
    Date of Patent: August 29, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Bernd Heiser, Hansjorg Stoller
  • Patent number: 4855423
    Abstract: Sulfatobetaines are prepared by reacting an addition compound of sulfur trioxide and a tertiary amine with an alkylene carbonate.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: August 8, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerold Braun, Chung-Ji Tschang, Christos Vamvakaris, Klaus Glaser
  • Patent number: 4845219
    Abstract: A compound of the general formula [I]: ##STR1## wherein R.sub.1 represents a higher alkyl group or an N-(higher alkyl)carbamoyl group, R.sub.2 represents a lower alkyl group, an acyl group having at least three carbon atoms, an N-(lower alkyl)carbamoyl group, an N-(lower alkyl)thiocarbamoyl group or a benzyl group, R represents a primary, secondary or tertiary amino group or a quaternary ammonium group, x is 1 or 2, y is a number of 0, 1 or 2, and z is an integer of 2-10, or a pharmaceutically acceptable salt thereof. The novel substances have both anti-tumor activity and platelet activating factor-inhibiting property, and they are effective as an anti-tumor agent without circulatory trouble.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: July 4, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Aono
  • Patent number: 4836958
    Abstract: The instant invention relates to fluorinated cationic compounds of the formula ##STR1## wherein R.sub.f is a perfluoroalkyl or perfluoroalkoxy-perfluoroalkyl group;R.sub.1 is alkylene optionally interrupted by --O--, --S--, --SO.sub.2 --, --SO.sub.2 NR'--, --CO.sub.2 --, --NR'--, or --CONR'-- where R' is hydrogen or lower alkyl;m is 0, 1 or 2;R.sub.2 is linear or branched alkylene;R.sub.3, R.sub.4, and R.sub.5 independently of one another represent alkyl or arylalkyl groups which are unsubstituted or substituted by hydroxyl, lower alkoxy, halogen, cyano or by polyalkyleneoxy, or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical or R.sub.3, R.sub.4 and R.sub.5 together with nitrogen atom that links them represent a substituted or unsubstituted pyridine ring; andA.sup..crclbar. represents the anion of an organic or inorganic acid; and their particular use as surfactants.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: June 6, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanasios Karydas
  • Patent number: 4820820
    Abstract: Cationic surface-active products of the formula:R.sub.1 --O[C.sub.2 H.sub.3 (R.sub.2)O--].sub.p [C.sub.2 H.sub.3 (CH.sub.2 OH)O].sub.(n-1) CH.sub.2 --CHOH--CH.sub.2 --Gin which R.sub.1 =C.sub.4 -C.sub.20 aliphatic radical, R.sub.2 =C.sub.4 -C.sub.20 alkyl, alkoxymethyl or alkenyloxy radical, p=1-2.5, n=2-20 and G denotes an amine or amine oxide group, and their salts are disclosed for use principally in cosmetics.
    Type: Grant
    Filed: September 23, 1987
    Date of Patent: April 11, 1989
    Assignee: L'Oreal
    Inventors: Henri Sebag, Guy Vanlerberghe
  • Patent number: 4772708
    Abstract: Derivatives of 4-hydroxy-methyl-piperidine having general formula: ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be alkyl or may form, with the carbon they are bound to, a cycloalkyl group or the group ##STR2## with R.sub.6, R.sub.7, R.sub.8 and R.sub.9 being hydrogen or alkyl; R.sub.5 may be H, alkyl, aryl, alkenyl, etc.; Y may be an organic or inorganic group or atom having a valence from 1 to 4 and n is an integer from 1 to 4.The use of the derivatives of the alkyl-substituted 4-hydroxy-methyl-piperidine of formula (I) as stabilizers of polymeric substances, and polymeric compositions stabilized with said piperdine derivatives.This invention relates to new derivatives of alkyl-substituted 4-hydroxy-methyl-piperidine, to the use thereof as stabilizers of polymeric substances usually subject to worsening owing to thermal and/or photo-oxidation, and to the polymeric compositions stabilized with said derivatives.
    Type: Grant
    Filed: March 20, 1987
    Date of Patent: September 20, 1988
    Assignee: Ausimont S.p.A.
    Inventors: Piero Di Battista, Gilberto Nucida
  • Patent number: 4772711
    Abstract: Disclosed is a method for the preparation of 3-aminoacrylic acid esters by the addition of a beta-hydroxyacrylic acid esters to an aqueous solution of an amine salt.
    Type: Grant
    Filed: August 19, 1986
    Date of Patent: September 20, 1988
    Assignee: Dynamit Nobel AG
    Inventors: Fritz Englaender, Moustafa El-chahawi, Wilhelm Vogt
  • Patent number: 4766119
    Abstract: p is an integer from one to three;NR is selected from the group consisting of pyrrolidino, piperidino, morpholino and dialkylamino containing a total of two to eight carbon atoms either straight chain or branched; or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: February 20, 1985
    Date of Patent: August 23, 1988
    Assignee: United Pharmaceuticals, Inc.
    Inventor: William M. Davis
  • Patent number: 4758564
    Abstract: Amines of the general formula ##STR1## where A is alkyl, alkenyl, cycloalkyl, cycloalkenyl, phenylalkyl or phenylalkenyl, X is oxygen or sulfur, B is an alkylene chain and R.sup.1 and R.sup.2 are each alkyl, alkenyl or cycloalkyl, or R.sup.1 and R.sup.2 form part of a heterocyclic structrure, and their salts, as well as fungicides containing these compounds.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: July 19, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Ernst Buschmann, Norbert Goetz, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4755599
    Abstract: The invention provides compounds of formula: ##STR1## in which R=H, halogen, alkyl, alkyloxy, alkythio, NH.sub.2, alkylamino, dialkylamino or CF.sub.3, R.sub.3 =H or alkyl,either R.sub.4 and R.sub.5 =H and R.sub.1 and R.sub.2 =H or alkyl, optionally substituted by alkenyl (2 to 4 C) or alternatively R.sub.1 and R.sub.2 form together a saturated heterocyclic ring containing 4 to 7 ring members and optionally containing another heteroatom such as O, S or N optionally substituted by alkyl,or R.sub.4 =H, R.sub.1 =H or alkyl and R.sub.2 and R.sub.5 together form an alkylene (3 to 4 C) radical and(i) either A=alkyl or phenyl which is unsubstituted or substituted by one or two substituents chosen from halogen, alkyl, alkyloxy, alkylthio, NH.sub.2, alkylamino, dialkylamino, NO.sub.2 or CF.sub.3 or alternatively A=pyridyl, benzyl or cycloalkyl (3 to 6 C), Y=S, SO or SO.sub.2 or a radical: ##STR2## in which R.sub.6 =H or alkyl and R.sub.
    Type: Grant
    Filed: February 3, 1987
    Date of Patent: July 5, 1988
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
  • Patent number: 4739066
    Abstract: Novel condensed seven-membered ring compounds of the formula: ##STR1## [wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, trifluoromethyl, lower alkyl or lower alkoxy, or both jointly form tri- or tetramethylene; R.sup.3 and R.sup.5 are independently hydrogen, lower alkyl or aralkyl; R.sup.4 is hydrogen or lower alkyl; R.sup.6 is a condensed or non-condensed hetero-alicyclic containing at least one atom of N, O and S as a ring-forming atom which may be substituted; A is an alkylene chain; n is 1 or 2] and salts thereof.These compounds exhibit inhibitory activity on angiotensin converting enzyme and so forth, and are of value as an agent for diagnosis, prevention and treatment of circulatory diseases, such as hypertension, cardiopathy and cerebral apoploxy.
    Type: Grant
    Filed: August 27, 1986
    Date of Patent: April 19, 1988
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirosada Sugihara, Kohei Nishikawa, Katsumi Ito
  • Patent number: 4731448
    Abstract: There is disclosed a process for the preparation of 1-(2-hydroxyethyl-2,2,6,6-tetramethyl-4-piperidinol from triacetoneamine, which comprises first reducing triacetoneamine in water and/or a polar organic solvent by catalytic hydrogenation to 2,2,6,6-tetramethyl-4-piperidinol, and adding a catalytic amount of acid to the resultant solution, without isolation of the intermediate, after optional concentration of the solution by distillation, and subsequently reacting the 2,2,6,6-tetramethyl-4-piperidinol with ethylene oxide.1-(2-Hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol is a useful light and heat stabilizer for plastics and is, in addition, a valuable intermediate for the synthesis of further light stabilizer additives.
    Type: Grant
    Filed: December 3, 1986
    Date of Patent: March 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Issler, Siegfried Kintopf, Lutz Konig, Hans Stephan
  • Patent number: 4695631
    Abstract: A process for the preparation of enamines or imines by isomerization of allylamine derivatives is described. Allylamine derivatives represented by formula (I): ##STR1## are isomerized using as a catalyst a rhodium complex represented by formula (IV):[Rh(olefin)L].sup.+ X.sup.- (IV)to form enamines or imines represented by, respectively, formula (II) or formula (III): ##STR2## All of the symbols in the above formulae are as described. These enamines or imines are useful intermediates for the preparation of a number of organic compounds.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: September 22, 1987
    Assignee: Takasago Perfumery Co., Ltd.
    Inventors: Seinosuke Otsuka, Kazuhide Tani, Tsuneaki Yamagata, Susumu Akutagawa, Hidenori Kumobayashi, Misao Yagi
  • Patent number: 4695653
    Abstract: Cationic surface-active agents which are polyhydroxylated tertiary amines or the quaternary ammonium salts thereof and which are usefully employed in cosmetic compositions, are prepared by condensing on a fatty alcohol, glycerol epihalohydrin alone or together with an epoxide to form polyhalogenated polyethers, which in turn are converted to polyhalogenated glycidyl ethers, the latter being reacted with a secondary amine to form polyhalogenated tertiary amines which are then reacted with sodium or potassium acetate in the presence of a diol to form said polyhydroxylated tertiary amines.
    Type: Grant
    Filed: August 23, 1983
    Date of Patent: September 22, 1987
    Assignee: L'Oreal
    Inventors: Gregoire Kalopissis, Guy Vanlerberghe
  • Patent number: 4661288
    Abstract: Water-soluble zwitterionic compounds having clay soil removal/anti-redeposition properties. The zwitterionic compounds are selected from monozwitterionic compounds, dizwitterionic compounds, polyzwitterionic compounds, and zwitterionic polymers. These zwitterionic compounds are useful in detergent compositions at from about 0.05 to about 95% by weight. In addition to the zwitterionic compounds, the detergent compositions further comprise from about 1 to about 75% by weight of a nonionic, anionic, ampholytic, zwitterionic, or cationic detergent surfactant or mixture thereof.
    Type: Grant
    Filed: March 8, 1985
    Date of Patent: April 28, 1987
    Assignee: The Procter & Gamble Company
    Inventors: Donn N. Rubingh, Eugene P. Gosselink
  • Patent number: 4650865
    Abstract: The invention relates to a process for preparing tertiary ether amines corresponding to the following general formula: ##STR1## by reacting in the presence of a strong base a tertiary amine corresponding to the following formula: ##STR2## with a sulfuric acid semi-ester salt corresponding to the following formula:R.sup.1 --(OC.sub.n H.sub.2n).sub.x --OSO.sub.3 M. (III)Preferably, each mole of the tertiary amine corresponding to formula (II) is reacted under substantially anhydrous conditions at a temperature of 140.degree. to 230.degree. C. with from about 0.2 to 3.0 moles of the sulfuric acid semi-ester salt of formula (III) in the presence of from about 1 to 1.5 moles of a strong base preferably an alkali metal hydroxide or an alkali metal alcoholate.
    Type: Grant
    Filed: February 7, 1986
    Date of Patent: March 17, 1987
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Fritz Lange, Alfred Meffert
  • Patent number: 4647562
    Abstract: A new class of anti-spasmodic compounds having three branch chains is provided. These compounds have the general formula: ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are saturated straight chain or branched alkyl groups contained from 1 to 8 carbon atoms, and are separated or linked to one another to form an aliphatic ring system. k is an integer from 0 to 5, and the total number of carbon atoms in R.sub.1 plus R.sub.2 plus R.sub.3 plus k are equal to or less than 12. Furthermore, l is an integer from 1 to 3, m is an integer from 1 to 3, n is an integer from 1 to 3, and X may be nonexistent or may be O, S, NH or CH.sub.2 or salts thereof. However, when X is nonexistent the terminal group in both the m chain and the n chain is a methyl group.
    Type: Grant
    Filed: February 20, 1985
    Date of Patent: March 3, 1987
    Assignee: United Pharmaceuticals, Inc.
    Inventor: William M. Davis
  • Patent number: 4596888
    Abstract: Novel monomers are the reaction products of a vinyl functional monoahl (e.g., hydroxypropyl acrylate) with a halohydroxyalkyl quaternary ammonium compound (e.g., 2-hydroxy-3-chloropropyl ammonium chloride) or a glycidyl trialkyl ammonium compound. Said monomers are highly hydrophilic. Polymers comprising said monomers have a very high affinity for water.
    Type: Grant
    Filed: September 1, 1983
    Date of Patent: June 24, 1986
    Assignee: The Dow Chemical Company
    Inventor: Walter L. Vaughn
  • Patent number: 4582904
    Abstract: Synthesis of organic amines by condensation of organic hydroxy compound with ammonia or a primary or secondary amine in the presence of a rare earth metal hydrogen phosphate catalyst.
    Type: Grant
    Filed: January 6, 1984
    Date of Patent: April 15, 1986
    Assignee: Air Products and Chemicals, Inc.
    Inventors: James E. Wells, Victoria Eskinazi
  • Patent number: 4582855
    Abstract: Novel compounds of the general formula ##STR1## wherein Ar represents a substituted or unsubstituted aromatic or heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, --NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1 wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or R.sub.1 and R.sub.3 may together with N form a 5 to 7 momoered heterocyclic group; and the pharmaceutically acceptable salts thereof. These compounds exhibit .beta.-adrenergic blocking activity and are also useful in the treatment of glaucoma.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: April 15, 1986
    Assignee: American Hospital Supply Corporation
    Inventors: Sheung T. Kam, William L. Matier
  • Patent number: 4578462
    Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## or --CH.sub.2 --CH.dbd.NR.sup.2 in which R.sup.2 and R.sup.3 represent lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring,by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen,is described.The compounds of formula I are potential intermediates in the manufacture of, inter alia, natural vitamin E and natural vitamin K.sub.1.
    Type: Grant
    Filed: August 22, 1983
    Date of Patent: March 25, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
  • Patent number: 4564698
    Abstract: The present invention relates to new tricyclic compounds of the formula: ##STR1## having valuable CNS and cardiovascular properties.
    Type: Grant
    Filed: January 24, 1983
    Date of Patent: January 14, 1986
    Assignee: Akzo N.V.
    Inventors: Johannes H. Wieringa, Frans A. van der Vlugt
  • Patent number: 4540523
    Abstract: Cationic styryl dyestuffs of the formula ##STR1## in which A.sup.1 is an alkyleneoxy or alkyleneamino radical,D.sup.1 is a direct bond or divalent radical,An is an anion, andthe terminal phenyl ring is unsubstituted or substituted by CN, alkyl or alkoxy. The compounds are suitable for dyeing, enscribing and printing paper for dyeing and printing synthetic fibres, especially made of polyacrylonitrile, acid-modified polyesters or polyamides.
    Type: Grant
    Filed: October 17, 1980
    Date of Patent: September 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hermann Beecken
  • Patent number: 4522945
    Abstract: Novel quinazoline derivatives, comprising in the heterocyclic part of their quinazoline nucleus at least one carbonyl or thiocarbonyl group and a particularly substituted piperidinyl-alkyl side chain, said compounds being potent serotonin-antagonists.
    Type: Grant
    Filed: March 26, 1982
    Date of Patent: June 11, 1985
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Jan Vandenberk, Ludo Kennis, Marcel Van der Aa, Albert Van Heertum
  • Patent number: 4482713
    Abstract: Novel quaternary ammonium salts of the general formula[R.sup.1 R.sup.2 R.sup.3 N(A--O).sub.n --R.sup.4 ].sup.+ Z.sup.-where R.sup.1 and R.sup.2 are identical or different and each is alkyl, aryl, aralkyl, alkylaryl, alkoxyalkyl, or a (poly)alkylene glycol radical, or R.sup.1 and R.sup.2, together with the nitrogen atom, are a heterocyclic ring, or one or more substituents R.sup.1 or R.sup.2 are polyfunctional so that the salt contains not less than 2 ammonium groups, R.sup.3 and R.sup.4 are identical or different monovalent radicals of one or more alkylating agents R.sup.3 X or R.sup.4 X, for example an (ar)alk(en)yl halide, sulfate or methosulfate or an (alkyl)aryl-sulfonate or -sulfonic acid ester, A is alkylene of 2 to 10 carbon atoms, n is an integer and Z is either X or another salt-forming anion or a hydroxyl ion, are prepared by N-alkylation and O-alkylation of an alkanolamine with the aid of a phase transfer catalyst and are useful as cationic surfactants, etc.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: November 13, 1984
    Assignee: BASF Aktiengesellschaft
    Inventor: Rainer Strickler
  • Patent number: 4436909
    Abstract: Cationic surface-active agents which are polyhydroxylated tertiary amines or the quaternary ammonium salts thereof and which are usefully employed in cosmetic compositions, are prepared by condensing on a fatty alcohol, glycerol epihalohydrin alone or together with an epoxide to form polyhalogenated polyethers, which in turn are converted to polyhalogenated glycidyl ethers, the latter being reacted with a secondary amine to form polyhalogenated tertiary amines which are then reacted with sodium or potassium acetate in the presence of a diol to form said polyhydroxylated tertiary amines.
    Type: Grant
    Filed: January 11, 1980
    Date of Patent: March 13, 1984
    Assignee: L'Oreal
    Inventors: Gregoire Kalopissis, Guy Vanlerberghe
  • Patent number: 4435330
    Abstract: Amphoteric branched sulfatobetaines of the formula ##STR1## wherein R.sub.f is perfluoroalkyl or perfluoroxyperfluoroalkyl; R.sub.1 is a direct bond or a divalent connecting group; R.sub.2, R.sub.3, and R.sub.4 are independently hydrogen or lower alkyl; R.sub.5, R.sub.6 and R.sub.7 are independently lower alkyl, and R.sub.6 may additionally represent aralkyl, and R.sub.6 and R.sub.7 taken together with the nitrogen to which they are attached may also represent piperidino or morpholino and R.sub.5, R.sub.6 and R.sub.7 taken together may also represent pyridyl, acridyl or quinolyl and salts thereof, their preparation and use as surfactants are disclosed.
    Type: Grant
    Filed: December 29, 1982
    Date of Patent: March 6, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert A. Falk
  • Patent number: 4435410
    Abstract: Compounds of the general formula: ##STR1## in which X represents a hydrogen or halogen atom, for example fluorine or chlorine, and R represents an alkyl group having 1 to 3 carbon atoms or alkenyl group having 2 to 3 carbon atoms are disclosed together with methods for their preparation and their use in the treatment of migraines, as anti-thrombosis agents or as rapid acting thymoanaleptic medicaments.
    Type: Grant
    Filed: May 3, 1982
    Date of Patent: March 6, 1984
    Assignee: Pharmindustrie
    Inventors: Gerard R. Le Fur, Christian L. A. Renault