Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Hetero Ring Patents (Class 540/529)
  • Patent number: 11390585
    Abstract: The invention provides heterocyclic compounds with quaternary centers and methods of preparing compounds. Methods include the method for the preparation of a compound of Formula (II): comprising treating a compound of Formula (I): with a transition metal catalyst and under alkylation conditions as valence and stability permit.
    Type: Grant
    Filed: February 1, 2021
    Date of Patent: July 19, 2022
    Assignee: California Institute of Technology
    Inventors: Brian M. Stoltz, Scott C. Virgil, David E. White, Taiga Yurino, Yiyang Liu, Douglas C. Behenna, Douglas Duquette, Christian Eidamshaus
  • Patent number: 8822679
    Abstract: A compound useful as a building block for the manufacture of various compounds is represented by Formula A or D. In Formula A and D, z is 0 or 1; Q is a heteroatom; R1 through R11 and Ra through Rf are each independently hydrogen, a substituted or unsubstituted hydrocarbyl group, a substituted or unsubstituted heteroatom containing hydrocarbyl group, or a functional group; d, e and f are each independently 0 or greater; each of A, B and D is independently a carbon atom or a heteroatom; and two or more of R1 though R11, Ra through Rf and Y optionally combine to form a ring. In some embodiments, R8 and R9 combine to form a carbonyl group. In some embodiments, R2 and Y combine to form a ring with the Q atom. In some embodiments, the ring includes at least one double bond.
    Type: Grant
    Filed: June 22, 2012
    Date of Patent: September 2, 2014
    Assignee: California Institute of Technology
    Inventors: Brian M Stoltz, Scott C. Virgil, David E White, Taiga Yurino, Yiyang Liu, Douglas C Behenna, Douglas Duquette, Christian Eidamshaus
  • Publication number: 20140024639
    Abstract: Compounds including various oligomers of piperlongumine and/or piperlongumine analogues as well as certain piperlongumine analogues that exhibit improved toxicity to cancer cells are disclosed. Also provided are compositions that comprise the compounds, methods of making compositions comprising the compounds, methods of making the compounds, and the use of compounds in methods for treating cancer.
    Type: Application
    Filed: July 19, 2013
    Publication date: January 23, 2014
    Inventors: Drew Adams, Mingji Dai, Stuart Schreiber, Mahmud Mustaqim Hussain, Zarko Boskovic
  • Publication number: 20130267699
    Abstract: The invention provides heterocyclic compounds with quaternary centers and methods of preparing compounds. Methods include the method for the preparation of a compound of Formula (II): comprising treating a compound of Formula (I): with a transition metal catalyst and under alkylation conditions as valence and stability permit.
    Type: Application
    Filed: March 12, 2013
    Publication date: October 10, 2013
    Inventors: Brian M. Stoltz, Scott C. Virgil, David E. White, Taiga Yurino, Yiyang Liu, Douglas C. Behenna, Douglas Duquette, Christian Eidamshaus
  • Publication number: 20130012701
    Abstract: A compound useful as a building block for the manufacture of various compounds is represented by Formula A or D. In Formula A and D, z is 0 or 1; Q is a heteroatom; R1 through R11 and Ra through Rf are each independently hydrogen, a substituted or unsubstituted hydrocarbyl group, a substituted or unsubstituted heteroatom containing hydrocarbyl group, or a functional group; d, e and f are each independently 0 or greater; each of A, B and D is independently a carbon atom or a heteroatom; and two or more of R1 though R11, Ra through Rf and Y optionally combine to form a ring. In some embodiments, R8 and R9 combine to form a carbonyl group. In some embodiments, R2 and Y combine to form a ring with the Q atom. In some embodiments, the ring includes at least one double bond.
    Type: Application
    Filed: June 22, 2012
    Publication date: January 10, 2013
    Applicant: California Institute of Technology
    Inventors: Brian M. Stoltz, Scott C. Virgil, David E. White, Taiga Yurino, Yiyang Liu, Douglas C. Behenna, Douglas Duquette, Christian Eidamshaus
  • Publication number: 20120277423
    Abstract: The present invention relates to: a ketone compound having transglutaminase-inhibiting activity, which is represented by the following Formula 1, 2, or 3: wherein R1 is a substituted or unsubstituted aryl or heterocyclyl group, R2, R3, and R4 are hydrogen atoms, n is 2, X is halogen, R5 and R6 independently represent a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl, aryl, or aralkyl group, wherein R5 and R6 are not hydrogen atoms at the same time, or R5 and R6 may be taken together to form a saturated or unsaturated and substituted or unsubstituted heterocyclyl group containing a nitrogen atom (N); an inhibitor of protein crosslinking comprising the compound; and a composition for preventing or treating a protein-crosslinking causative disease, which comprises the compound or the protein crosslinking inhibitor.
    Type: Application
    Filed: May 19, 2010
    Publication date: November 1, 2012
    Inventors: Katsuhiko Mikoshiba, Kozo Hamada, Akiko Terauchi, Shouichirou Ozaki, Jun-ichi Goto, Etsuko Ebisui, Akinobu Suzuki
  • Publication number: 20090124601
    Abstract: Tartaric acid salts of (3R)-4-[(3R)-3-amino-4-(2,4,5-trifluorophenyl) butanoyl]hexahydro-3-(2,2,2-trifluoroethyl)-2H-1,4-diazepin-2-one are potent inhibitors of dipeptidyl peptidase-IV and are useful for the prevention and/or treatment of non-insulin dependent diabetes mellitus, also referred to as Type 2 diabetes. The invention also relates to crystalline anhydrate forms of the tartaric acid salts as well as a process for their preparation, pharmaceutical compositions containing these novel forms and methods of use for the treatment of Type 2 diabetes.
    Type: Application
    Filed: March 24, 2006
    Publication date: May 14, 2009
    Inventors: Zhiguo J. Song, Fei Zhang, Rebecca Leigh Shultz
  • Patent number: 6914140
    Abstract: A novel process for the manufacture of compounds of the formula wherein R1 and R2 independently represent aroyl. The present invention also concerns novel intermediates used in the novel process for making compounds of formula I.
    Type: Grant
    Filed: April 10, 2000
    Date of Patent: July 5, 2005
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Peter Karl Matzinger, Michelangelo Scalone, Ulrich Zutter
  • Publication number: 20030220318
    Abstract: Specific phenylalanine derivatives or pharmaceutically acceptable. salts thereof have an antagonistic effect on the &agr;4 integrins and, therefore, are usable as therapeutic agents or preventive agents for diseases in which &agr;4 integrin-depending adhesion process participates in the pathology, such as inflammatory diseases, rheumatoid arthritis, inflammatory bowel diseases, systemic lupus erythematosus, multiple sclerosis, Sjögren's syndrome, asthma, psoriasis, allergy, diabetes, cardiovascular diseases, arterial sclerosis, restenosis, tumor proliferation, tumor metastasis and transplantation rejection.
    Type: Application
    Filed: March 31, 2003
    Publication date: November 27, 2003
    Applicant: AJINOMOTO CO. INC
    Inventors: Nobuyasu Suzuki, Toshihiko Yoshimura, Hiroyuki Izawa, Kazuyuki Sagi, Shingo Makino, Eiji Nakanishi, Masahiro Murata, Takashi Tsuji
  • Publication number: 20030027771
    Abstract: Disclosed are pyroglutamic acid derivatives and related compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.
    Type: Application
    Filed: May 7, 2002
    Publication date: February 6, 2003
    Inventors: Darren B. Dressen, Anthony Kreft, Dennis Kubrak, Charles William Mann, Michael A. Pleiss, Gary Paul Stack, Eugene D. Thorsett
  • Patent number: 6486151
    Abstract: This invention relates to neurotrophic low molecular weight, small molecule N-oxides of heterocyclic esters amides, thioesters, and ketones having an affinity for FKBP-type immunophilins, and their use as inhibitors of the enzyme activity associated with immunophilin proteins, particularly peptidyl-prolyl isomerase, or rotamase, enzyme activity.
    Type: Grant
    Filed: April 26, 2001
    Date of Patent: November 26, 2002
    Assignee: GPI NIL Holdings Inc.
    Inventors: Gregory S. Hamilton, Joseph P. Steiner, Eric S. Burak
  • Patent number: 6458781
    Abstract: The present invention provides compounds that block calcium channels and have the Formula I: The present invention also provides pharmaceutical compositions containing the compounds of Formula I and methods of using them to treat stroke, cerebral ischemia, head trauma, and epilepsy.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: October 1, 2002
    Inventors: David Thomas Connor, Lain-Yen Hu, Thomas Charles Malone, Michael Francis Rafferty, Bruce David Roth, Todd Robert Ryder, Anthony Denver Sercel, Yuntao Song
  • Patent number: 6268530
    Abstract: Process to separate linear 5-formylvaleric acid from a mixture of 5- and 3- and 4-formylvaleric acids, wherein the separation is performed by fractional extraction with two immiscible solvents of which one solvent is an aqueous solvent and the other solvent is an organic solvent, in which the organic solvent has a higher or lower affinity for 5-formylvaleric acid than its affinity for the 3-formylvaleric acids and for the 4-formylvaleric acid. Furthermore the invention relates to an improved process to prepare ∈-caprolactam starting from a mixture of branched and linear formylvaleric acids or starting from pentenoic acid.
    Type: Grant
    Filed: January 5, 1998
    Date of Patent: July 31, 2001
    Assignees: DSM N.V., E. I. DuPont de Nemours and Company
    Inventors: Imre Toth, Onko Gelling, Rudolf P. M. Guit, Antonius J. F. Simons, Simon Hans H. Niemann
  • Patent number: 6251892
    Abstract: This invention relates to neurotrophic low molecular weight, small molecule N-oxides of heterocyclic esters, amides, thioesters, and ketones having an affinity for FKBP-type immunophilins, and their use as inhibitors of the enzyme activity associated with immunophilin proteins, particularly peptidyl-prolyl isomerase, or rotamase, enzyme activity.
    Type: Grant
    Filed: April 21, 2000
    Date of Patent: June 26, 2001
    Assignee: GPI NIL Holdings, Inc.
    Inventors: Gregory S. Hamilton, Joseph P. Steiner, Eric S. Burak
  • Patent number: 6160126
    Abstract: Novel Intermediates ##STR1## wherein R is a substituted or unsubstituted hydrocarbon residue or acyl group; X is an electron withdrawing group; Y.sup.1 and Y.sup.2, which are the same or different, are each independently oxygen or sulfur; and A is a substituted or unsubstituted, divalent hydrocarbon residue have potent reactivity, this being useful in preparing guanidine derivatives.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: December 12, 2000
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yasuyuki Kando, Hideki Uneme, Isao Minamida
  • Patent number: 6069245
    Abstract: A novel process for the manufacture of compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 independently represent aroyl. The present invention also concerns novel intermediates used in the novel process for making compounds of formula I.
    Type: Grant
    Filed: November 19, 1998
    Date of Patent: May 30, 2000
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Peter Karl Matzinger, Michelangelo Scalone, Ulrich Zutter
  • Patent number: 6054452
    Abstract: This invention relates to neurotrophic low molecular weight, small molecule N-oxides of heterocyclic esters, amides, thioesters, and ketones having an affinity for FKBP-type immunophilins, and their use as inhibitors of the enzyme activity associated with immunophilin proteins, particularly peptidyl-prolyl isomerase, or rotamase, enzyme activity.
    Type: Grant
    Filed: July 9, 1998
    Date of Patent: April 25, 2000
    Assignee: GPI NIL Holdings, Inc.
    Inventors: Gregory S. Hamilton, Joseph P. Steiner, Eric S. Burak
  • Patent number: 6054579
    Abstract: The invention relates to an efficient and facile method for the preparation of substituted lactams, as described herein. The method comprises reacting a difunctional component containing an activated carbon, an amine capable of forming an imine with the activated carbon of the difunctional component, and an isocyanide in a nucleophilic polar protic solvent and at a concentration of reactants which facilitates the formation of the substituted lactams. The invention also relates to novel substituted lactams, libraries comprising such lactams, and a method of generating libraries substituted lactams, using the method of the invention.
    Type: Grant
    Filed: June 19, 1998
    Date of Patent: April 25, 2000
    Assignee: LeukoSite, Inc.
    Inventor: Geraldine C. B. Harriman
  • Patent number: 6028192
    Abstract: The present invention relates to a process for the preparation of compounds of the formula 1 ##STR1## by reacting a secondary acid amide of the formula 2 ##STR2## with an acid chloride of the formula 3 ##STR3## in the presence of N,N-diisopropyl-N-ethylamine. R.sup.1, R.sup.2 and R.sup.3 are alkyl or alkenyl radicals, if required also aryl radicals. The compounds of the formula 1 are suitable for use as insecticides or bleach activators.
    Type: Grant
    Filed: January 27, 1998
    Date of Patent: February 22, 2000
    Assignee: Clariant GmbH
    Inventors: Johannes Becherer, Klaus Delpy, Karl-Heinz Keil, Bernhard Mees
  • Patent number: 6013606
    Abstract: Substituted cinnamic oxime derivatives I and cinnamic hydroxamide derivatives II ##STR1## (R.sup.1= halogen, NO.sub.2, CN, CF.sub.3 ; R.sup.2 =H, halogen; R.sup.3= H, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, hydroxy-C.sub.1 -C.sub.6 -alkyl;R.sup.4= H, halogen, CN, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl orR.sup.3 +R.sup.4 =chemical bond;Y=--O--, --S--, --O--CO--, --O--SO.sub.2 -- or chemical bond;Y'=--O-- or --S--;R.sup.5= unsubst. or subst. C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, unsubst. or subst. phenyl or phenyl-C.sub.1 -C.sub.6 -alkyl, or, if Y is --O--, --S-- or a chemical bond, is (C.sub.1 -C.sub.6 -alkyl)carbonyl or (C.sub.1 -C.sub.6 -alkoxy)carbonyl; or, if Y is a chemical bond, is hydrogen or halogen;R.sup.5 '=R.sup.5, H or (C.sub.1 -C.sub.6 -haloalkyl)carbonyl;R.sup.6= H, C.sub.1 -C.
    Type: Grant
    Filed: June 30, 1997
    Date of Patent: January 11, 2000
    Assignee: BASF Akteingesellschaft
    Inventors: Ralf Klintz, Gerhard Hamprecht, Elisabeth Heistracher, Peter Schafer, Christoph-Sweder von dem Bussche-Hunnefeld, Peter Munster, Reinhard Kirstgen, Albrecht Harreus, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
  • Patent number: 5902882
    Abstract: A novel process for the manufacture of compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 independently represent aroyl. The present invention also concerns novel intermediates used in the novel process for making compounds of formula I.
    Type: Grant
    Filed: April 3, 1997
    Date of Patent: May 11, 1999
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Peter Karl Matzinger, Michelangelo Scalone, Ulrich Zutter
  • Patent number: 5856318
    Abstract: Certain nitrogen-containing cyclohetero cycloalkylaminoaryl compounds are described for treatment of CNS disorders such as cerebral ischemia, psychoses and convulsions. Compounds of particular interest are of the formula: ##STR1## wherein each of R.sup.1, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 is independently selected from hydrido, lower alkyl, benzyl, and haloloweralkyl;wherein each of R.sup.2, R.sup.3 and R.sup.8 through R.sup.11 is independently selected from hydrido, hydroxy, loweralkyl, benzyl, phenoxy, benzyloxy and haloloweralkyl; wherein n is an integer of from four to six; wherein m is an integer of from two to four; wherein A is selected from phenyl, naphthyl, benzothienyl, benzofuranyl and thienyl; wherein any of the foregoing A groups can be further substituted with one or more substituents independently selected from hydrido, hydroxy, loweralkyl, loweralkoxy, halo, haloloweralkyl, amino, monoloweralkylamino and diloweralkylamino; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: August 11, 1997
    Date of Patent: January 5, 1999
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Wayne Bowen, Brian R. de Costa, Celia Dominguez, Xiao-Shu He, Kenner C. Rice
  • Patent number: 5847123
    Abstract: Imide compounds having a propioloyl group or pharmaceutically acceptable salts thereof which exhibit potent activities to inhibit the production of Interleukin 1-.beta. and also the production of Tumor Necrosis Factor .alpha.. These imide compounds are useful as a prophylactic or therapeutic agent for inhibiting the production of Interleukin 1-.beta. and the production of Tumor Necrosis Factor .alpha., typically for such diseases as chronic rheumatism, sepsis, ulcerative colitis, Crohn's disease and many other related diseases in which Interleukin 1-.beta. and/or Tumor Necrosis Factor .alpha. would participate.
    Type: Grant
    Filed: July 1, 1997
    Date of Patent: December 8, 1998
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Shinji Yokoyama, Noriyoshi Sueda, Hiroaki Yamada, Ryotaro Kojima, Koichi Katsuyama
  • Patent number: 5688944
    Abstract: The present invention provides a novel carbamazepine hydrazide compound suitable for covalent attachment to a polymer particle reagent, having the general formula ##STR1## The present invention also provides a novel carbamazepine acid compound suitable for attachment to proteins for the production of carbamazepine immunogens. The carbamazepine antigen of the present invention has the following general structure: ##STR2## where X is C.dbd.O, CH.sub.2 or SO.sub.2 ; Y is C.dbd.O, CH.sub.2, SO.sub.2 ; R is an alkyl and P is a protein or a hapten.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: November 18, 1997
    Assignee: Dade International Inc.
    Inventor: Chengrong Wang
  • Patent number: 5677444
    Abstract: A novel and simple method is proposed for the synthetic preparation of an N,N-disubstituted .beta.-ketothioamide compound represented by the general formulaR.sup.1 R.sup.2 N--CS--CH.sub.2 --CO--R.sup.3,in which R.sup.1 and R.sup.2 are each a monovalent hydrocarbon group or each a divalent hydrocarbon group jointly forming a cyclic structure together with the nitrogen atom and R.sup.3 is a hydrogen atom, a monovalent hydrocarbon group or a divalent hydrocarbon group forming a cyclic structure jointly with R.sup.1, R.sup.1 being a divalent hydrocarbon group and R.sup.2 being a monovalent hydrocarbon group. The method comprises:(a) mixing an N,N-disubstituted amide compound represented by the general formulaR.sup.1 R.sup.2 N--CO--R.sup.3,and a bis(trialkylsilyl)thioketene compound represented by the general formula(R.sub.3 Si).sub.2 C.dbd.C.dbd.
    Type: Grant
    Filed: September 15, 1995
    Date of Patent: October 14, 1997
    Assignee: Japan as represented by Director General of Agency of Industrial Science and Technology
    Inventors: Tohru Tsuchiya, Isao Shibuya, Yoichi Taguchi, Akihiro Oishi, Kazumasa Honda
  • Patent number: 5594134
    Abstract: A process of synthesizing N-acyl auxiliary compounds is disclosed. A compound of the formula: ##STR1## is reacted with an anhydride in the presence of a lithium salt and an amine base to produce the N-acylated auxiliary.
    Type: Grant
    Filed: March 31, 1995
    Date of Patent: January 14, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Guo-Jie Ho, David J. Mathre
  • Patent number: 5510477
    Abstract: High quality acyl lactam imides are prepared by reacting an acyl lactam of the formula ##STR1## where 5 carbon atoms and an acylating acid of the formula R'CO.sub.2 H or by reacting a lactam, an anhydride of the formula (RCO).sub.2 O where R is 1 to 5 carbon atoms and an acylating acid, preferably in the presence of a base catalyst. The process affords acyl lactam imides in high yield and at lower reaction temperatures by providing for the removal of volatile carboxylic acid by-products under vacuum or by the use of a stripping gas. The acyl lactam imides are particularly suited for use as bleach activators in detergent compositions.
    Type: Grant
    Filed: March 1, 1994
    Date of Patent: April 23, 1996
    Assignee: The Procter & Gamble Company
    Inventors: Alan D. Willey, Larry E. Miller
  • Patent number: 5308520
    Abstract: Various heterocyclic compounds have been discovered that impart improved fuel economy and friction modification to lubricant and fuel compositions. These heterocyclic compounds of the invention preferably contain nitrogen and may be further reacted with hydrocarbyl carboxylic acid acylating reactants or hydrocarbyl phenolic reactants to give higher molecular materials. These higher molecular weight materials have higher oil-solubility and impart dispersancy properties to lubricant and fuel compositions.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: May 3, 1994
    Assignee: The Lubrizol Corporation
    Inventors: Joseph W. Pialet, Paul E. Adams
  • Patent number: 5155102
    Abstract: 1-alkyl-3-(acylamino)-.epsilon.-caprolactames of formula (1) ##STR1## wherein R is selected from the group consisting of:pyrrolidin-2-one-1-acetyl,p-methoxybenzoyl,N-benzyloxycarbonyl-(S)-prolyl,phenylbutanoyl,3-trifluoromethylbenzoyl,3,4,5-trimethoxybenzoyl,nicotinoyl, andacyl having from 1 to 5 carbon atoms, andR.sub.1 is selected from the group consisting of:hydrogen,methoxycarbonylmethyl,aminocarbonylmethyl,2-hydroxyethyl, andformylmethyl,(provided that, if R.sub.1 is hydrogen, R is not formyl or acetyl) are potent enhancers of learning and memory.Orally or parenterally administrable pharmaceutical compositions in unit dosage form comprise from about 100 to 500 mg of one of the compound of formula (1).
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: October 13, 1992
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Fabio Giannessi, Orlando Ghirardi, Domenico Misiti, Maria O. Tinti, Roberto Cozzolino, Carlo Scolastico
  • Patent number: 5153316
    Abstract: The present invention relates to novel phenylimidazolone compounds of the formula ##STR1## wherein A is a bond or C.dbd.T;R is --H, Alk, halo-Alk, cyano-Alk, or phenyl;R.sup.1 is --H, Alk, halogen, halo-Alk, --CN; or when A is a bond, R and R.sup.1 may together form a saturated, partially saturated, or unsaturated three to seven member carbon ring, and the ring may be substituted at any position independently with one or more Alk, --O--Alk, --CN, halogen, --OH, or .dbd.O groups;T is O or S;U is --H;V is --OH, or U and V may together form a bond;W is halogen or --CN, and when W is halogen, R.sup.1 is --CN;X is --H or halogen;Y is --H, halogen, --CN, Alk, --CF.sub.3, or --OCF.sub.3 ;Z is --H, halogen, --OH, Alk, aryloxy, C.sub.1-6 acyl, --NH.sub.2, --NO.sub.2, --NR.sup.2 SO.sub.2 R.sup.2, --N(SO.sub.2 R.sup.2).sub.2, --NR.sup.2 COR.sup.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: October 6, 1992
    Inventors: Gary D. Crouse, Michael P. Lynch, Jeffery D. Webster, John P. Wright
  • Patent number: 5142044
    Abstract: This invention relates to a method for administering systemically active agents including therapeutic agents through the skin or mucosal membranes of humans and animals in a transdermal device or formulation comprising topically administering with said systemic agent an effective amount of a membrane penetration enhancer having the structure formula ##STR1## wherein X and Y, each, may represent sulfur, oxygen or two hydrogen atoms, A is a branched or a straight chain, divalent aliphatic radical having from 0 to 2 double bonds; R' is selected from the group consisting of H, a lower alkyl group having 1-4 carbon atoms, phenyl, lower alkyl or halogen substituted phenyl, acetamido, halogen, piperidinyl, lower alkyl or halogen substituted piperidinyl, carbalkoxy, carboxamide, and alkylformyl; m is 3-7; q is 2m-2x, wherein x equals the number of double bonds in the lactam ring and may be 1, 2 or 3, and R is CH.sub.3, ##STR2## or ##STR3## wherein R" is H or halogen.
    Type: Grant
    Filed: January 22, 1990
    Date of Patent: August 25, 1992
    Assignee: Whitby Research, Inc.
    Inventors: Gevork Minaskanian, James V. Peck
  • Patent number: 5116958
    Abstract: Disperse dyes, which produce dyeings of excellent thermomigration fastness, consisting of a chromophore and a lactam or oxime radical which detaches on heating to leave an isocyanate or isothiocyanate group, which reacts with a suitable group in the environment. The disclosed dyes are described by the formula ##STR1## where F is the radical of a dye which is free of water-solubilizing groups,B is a bridge member or a direct bond,Z is O or S andV is the radical of a group H--V, where H--V is an oxime of the formula ##STR2## or a lactam of the formula ##STR3## in which R.sup.1 and R.sup.2 are each independently of the other substituted or unsubstituted alkyl or aryl, orR.sup.1 and R.sup.2 together with the carbon atom linking them form a cycloaliphatic ring,R is hydrogen or alkyl andn is an integer from 4 to 11.
    Type: Grant
    Filed: January 5, 1990
    Date of Patent: May 26, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Liechti, Martin Trottmann
  • Patent number: 5093031
    Abstract: The invention relates to properties and uses of N-hydrocarbon substituted lactams, particularly N-alkyl substituted lactams having the formula ##STR1## wherein R' is a hydrophobic radical such as linear or branched chain alkyl group containing from 8 to 27 carbon atoms, most preferably micelle forming pyrrolidones having 12 to 16 carbon atoms in the R' group. The invention particularly relates to the uses of the N-hydrocarbon substituted lactams which involve surfactant properties, such as solubility, wetting, viscosity building, emulsifying and/or complexing properties.
    Type: Grant
    Filed: October 14, 1988
    Date of Patent: March 3, 1992
    Assignee: ISP Investments Inc.
    Inventors: Robert B. Login, Ratan K. Chaudhuri, Rama K. Haldar, Mohamed M. Hashem, Michael W. Helioff, David J. Tracy
  • Patent number: 5059687
    Abstract: A process for the condensation of imides and alcohols or amines to ester acyl lactams, ester amide acyl lactams or amide acyl lactams by reacting a polyol or polyamine in the liquid phase with an acyl lactam compound is disclosed.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: October 22, 1991
    Assignee: Stamicarbon B.V.
    Inventors: Christiaan Schroder, Albert A. Van Geenen, Josefina M. A. Schiffer
  • Patent number: 5043441
    Abstract: This invention provides compositions comprising a physiologically-active agent and a compound having the structural formula ##STR1## wherein each X, Y and Z may represent oxygen, sulfur or two hydrogen atoms, provided however that, when Z represents two hydrogen atoms, both X and Y represent oxygen or sulfur and when Z represents oxygen or sulfur at least one of X and Y must represent oxygen or sulfur; m is 2-6; R' is H or a lower alkyl group having 1-4 carbon atoms; n is 0-17 and R is --CH.sub.3, ##STR2## wherein R" is H or halogen in an amount effective to enhance the penetration of the physiologically-active agent through the skin or other membrane of the body of an animal.
    Type: Grant
    Filed: January 22, 1990
    Date of Patent: August 27, 1991
    Assignee: Whitby Research, Inc.
    Inventors: James V. Peck, Gevork Minaskanian
  • 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: 5021439
    Abstract: A compound having the formula (I) or (II) ##STR1## wherein R.sup.1 is a hydrogen atom or an organic residue bonded via a carbon atom, R.sup.2 is a hydrogen atom or a N-protecting group, --COR.sup.3 is an optionally esterified or amidated carboxyl group, R.sup.4 and R.sup.5 are the same or different and respectively a hydrogen atom or an acyl group or a chain or alicyclic hydrocarbon group optionally having an aryl substituent, R.sup.6 is NOH or O, n is an integer of 0 to 3, or R.sup.4 and R.sup.5 together with the adjacent nitrogen atom may form a ring or an optionally substituted benzylidene amino group, which is useful therapeutics of brain dysfunction.
    Type: Grant
    Filed: September 18, 1989
    Date of Patent: June 4, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Setsuo Harada, Akinobu Nagaoka, Katsumi Itoh, Shinji Terao
  • Patent number: 4970306
    Abstract: The invention relates to trans-cyclohexane-1,4-diisocyanate which is completely or partially blocked with epsilon-caprolactam and a method of manufacturing the same wherein 1 mole trans-cyclohexane-1,4-diisocyanate is reacted with 1 to 2 moles epsilon-caprolactam, without or with the presence of solvents. These blocked diisocyanates are used for polyurethane powders.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: November 13, 1990
    Assignee: Huels Aktiengesellschaft
    Inventors: Rainer Gras, Elmar Wolf
  • Patent number: 4801586
    Abstract: This invention relates to a method for administering systemically active agents including therapeutic agents through the skin or mucosal membranes of humans and animals in a transdermal device or formulation comprising topically administering with said systemic agent an effective amount of a membrane penetration enhancer having the structural formula ##STR1## wherein X and Y, each, may represent sulfur, oxygen or two hydrogen atoms, A is a branched or a straight chain, divalent aliphatic radical having from 0 to 2 double bonds; R' is selected from the group consisting of H, a lower alkyl group having 1-4 carbon atoms, phenyl, lower alkyl or halogen substituted phenyl, acetamido, halogen, piperidinyl, lower alkyl or halogen substituted piperidinyl, carbalkoxy, carboxamide, and alkylformyl; m is 3-7; q is 2m-2x, wherein x equals the number of double bonds in the lactam ring and may be 1, 2 or 3, and R is CH.sub.3, ##STR2## wherein R" is H or halogen.
    Type: Grant
    Filed: October 7, 1986
    Date of Patent: January 31, 1989
    Assignee: Nelson Research & Development Co.
    Inventors: Gevork Minaskanian, James V. Peck
  • Patent number: 4784782
    Abstract: Various heterocyclic compounds have been discovered that impart improved fuel economy and friction modification to lubricant and fuel compositions. These hetrocyclic compounds of the invention preferably contain nitrogen and may be further reacted with hydrocarbyl carboxylic acid acylating reactants or hydrocarbyl phenolic reactants to give higher molecular materials. These higher molecular weight materials have higher oil-solubility and impart dispersancy properties to lubricant and fuel compositions.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: November 15, 1988
    Assignee: The Lubrizol Corporation
    Inventors: Joseph W. Pialet, Paul E. Adams
  • Patent number: 4755535
    Abstract: This invention provides compositions comprising a physiologically-active agent and an azacycloalkene having at least one double bond in the ring and of the general formula ##STR1## wherein X and Y, each, may represent sulfur, oxygen or two hydrogen atoms, A is a straight or branched chain, divalent aliphatic radical having from 0 to 2 double bonds; R' is selected from the group consisting of H, a lower alkyl group having 1-4 carbon atoms, phenyl, lower alkyl or halogen substituted phenyl, acetamido, halogen, piperidinyl, lower alkyl or halogen substituted piperidinyl, carbalkoxy, carboxamide, and alkylformyl; m is 3-7; q is 2m-2x, wherein x equals the number of double bonds in the lactam ring and may be 1, 2 or 3; and R is --CH.sub.3, ##STR2## wherein R" is H or halogen in an amount effective to enhance the penetration of the physiologically-active agent through the skin or other membrane of the body of an animal.
    Type: Grant
    Filed: April 23, 1986
    Date of Patent: July 5, 1988
    Assignee: Nelson Research & Development Co.
    Inventors: Gevork Minaskanian, James V. Peck
  • Patent number: 4692521
    Abstract: The invention relates to N-substitutecd acyl lactam compounds of the formula ##STR1## where R is a polyol residue originating from a polyol with the formula R-(OH).sub.x where x is a number.ltoreq.2R' a bivalent cyclic or non-cyclic alkyl, aralkyl, alkaryl or aryl radicalR" a bivalent radical having the following general formula ##STR2## wherein R'" is H, alkyl, cycloalkyl, aryl, alkaryl or aralkyl,R.sup.iv is H, alkyl, cycloalkyl, aryl, alkaryl or aralkyl whereR"' and R.sup.iv may jointly form a substituted or non-substituted cycloalkyl residuen is 0 or 1 and(-L) represents a non-opened lactam ring of the formula ##STR3## wherein Y is hydrocarbon residue with 3-11 carbon atoms. It has been found that this group of compounds is very suitable as activator in the preparation of nylon block copolymers, more specifically in the RIM or RRIM systems.
    Type: Grant
    Filed: December 13, 1985
    Date of Patent: September 8, 1987
    Assignee: Stamicarbon B.V.
    Inventors: Jozef J. M. Bongers, Albert A. Van Geenen
  • Patent number: 4692520
    Abstract: The invention relates to the N-substituted acyl-lactam compound of the formula: ##STR1## where R' is a bivalent cyclic or non-cyclic alkyl, aralkyl, alkaryl or aryl radicalR" a bivalent radical having the following general formula ##STR2## wherein R'" is H, alkyl, cycloalkyl, aryl, alkaryl or aralkyl,R.sup.iv is H, alkyl, cycloalkyl, aryl, alkaryl or aralkyl whereR'" and R.sup.iv may jointly form a substituted or non-substituted cycloalkyl residuen is 0 or 1(-L) represents a non-opened lactam ring andx a number>1.It has been found that this group of compounds is very suitable as activator in the preparation of nylon polymers, more specifically in the so-called RIM (Reaction Injection Moulding) or RRIM (reinforced RIM) systems, in which it is highly essential for the polymerization to take effect within a very short time.
    Type: Grant
    Filed: December 13, 1985
    Date of Patent: September 8, 1987
    Assignee: Stamicarbon B.V. (Subsidiary of DSM)
    Inventors: Albert A. Van Geenen, Jozef J. M. Bongers
  • Patent number: 4683304
    Abstract: The invention relates to a process for preparing an acyl-lactam compound characterized in that the reaction product of a lactam with a dicarboxylic acid anhydride is reacted with a polyol at a temperature of 150.degree. C. at most. These acyl-lactam compounds are very suitable as activator in the preparation of nylon block copolymers, more specifically in the RIM or RRIM systems.
    Type: Grant
    Filed: December 13, 1985
    Date of Patent: July 28, 1987
    Assignee: Stamicarbon B.V.
    Inventors: Albert A. Van Geenen, Jozef J. M. Bongers
  • Patent number: 4644051
    Abstract: The invention concerns a simple process for preparing an ester acyllactam and/or esteramide acyllactam by the catalytic condensation of imide and alcohol, characterized in that a polyol and an acyllactam compound are reacted in the liquid state in the presencce of a halide, carboxylate or acetylacetonate from beryllium, magnesium, calcium, strontium, barium, boron, aluminium, zinc or cadmium.The invention is important for the preparation of compounds which may be used in the preparation of nylon block copolymers, more in particular in RIM-nylon systems (Reaction Injection Moulding), since when the compounds obtained according to the present invention are used in a RIM system, a very fast lactam polymerization takes place, and it therefore also relates to the preparation of nylon block copolymers.
    Type: Grant
    Filed: December 26, 1984
    Date of Patent: February 17, 1987
    Assignee: Stamicarbon B.V.
    Inventor: Albert A. Van Geenen
  • Patent number: 4608201
    Abstract: A process for preparing a lactam imide involves reacting together a lactam, a non-volatile carboxyl group-containing material, and an anhydride of a volatile carboxylic acid with the proviso that an appreciable amount of non-volatile carboxyl group-containing material and volatile carboxylic acid which is generated as the anhydride reacts are both present in the reaction mixture at the same time.
    Type: Grant
    Filed: May 21, 1984
    Date of Patent: August 26, 1986
    Assignee: PPG Industries, Inc.
    Inventor: Gregory J. McCollum