Nitrogen Attached Directly Or Indirectly To The Five-membered Hetero Ring By Acyclic Nonionic Bonding Patents (Class 548/550)
  • Patent number: 5202344
    Abstract: This invention relates to novel N-substituted lactams having the following formula ##STR1## useful in the treatment and prevention of Cholecystokinin (CCK) related disorders of the gastrointestinal, central nervous and appetite regulatory systems of mammals.
    Type: Grant
    Filed: December 11, 1990
    Date of Patent: April 13, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Daniel P. Becker, Daniel L. Flynn, Clara I. Villamil
  • Patent number: 5191089
    Abstract: Herbicidal 4-alkoxy- and 4-(substituted)amino-arylpyrrolinone derivatives of the formula ##STR1## in which X and Y independently of one another represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl or in each case unsubstituted or substituted aryloxy or arylthio,Z represents halogen, alkyl or alkoxy,n represents the number 0, 1, 2 or 3,A represents in each case unsubstituted or in each case halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, cycloalkyl which is optionally interrupted by hetero atoms, arylalkyl which is unsubstituted or substituted by halogen, alkyl, halogenoalkyl, alkoxy and/or nitro, unsubstituted aryl or aryl substituted by a member selected from the group consisting of halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy and phenoxy or phenylthio which are in each case unsubstituted or substituted by halogen, alkyl, alkoxy, halogenoalkyl and/or halogenoalkoxy,B represents hydroxyl, alkoxy, halogenoalkoxy or cycloalkoxy, the cycloalkyl radical b
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: March 2, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Baasner, Reiner Fischer, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt
  • Patent number: 5177069
    Abstract: The present invention provides a novel class of naphthylsulfonylalkanoic acid compounds such as a structure corrresponding to the formula: ##STR1## or a pharmaceutically acceptable salt thereof. A present invention naphthylsulfonylalkanoic acid compound is useful for prevention or treatment of irritable bowel syndrome, biliary dyskinesia and acute pancreatitis.
    Type: Grant
    Filed: December 6, 1990
    Date of Patent: January 5, 1993
    Assignee: Kissei Pharmaceutical Co., Ltd.
    Inventors: Makio Kitazawa, Masuo Akahane, Yasushi Nakano, Atsushi Tsubaki, Kazuaki Sato, Masaaki Ban, Michihiro Kobayashi
  • Patent number: 5157126
    Abstract: A solution of stearamidopropyl dimethyl pyrrolidonyl methyl ammonium chloride in a polyhydric alcohol, suitably at a concentration of about 1-30% by weight, preferably 2-20%, and, optimally, about 5-15%, wherein said polyhydric alcohol is a di-, tri-, or tetra hydric alcohol, preferably glycerol, is prepared by(a) slurrying said compound into excess acetone,(b) filtering the slurry to provide a filter cake of said compound,(c) forming a solution of said filter cake in a polyhydric alcohol, and(d) dropping said solution into an evacuated reaction vessel at a suitable rate to minimize excessive foaming while residual acetone is removed therefrom, the solution remaining under substantial full vacuum until substantially all the solution has been added and substantially of the acetone has been removed.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: October 20, 1992
    Assignee: ISP Investments Inc.
    Inventors: Lowell R. Anderson, Ratan K. Chaudhuri, Robert B. Login
  • Patent number: 5151536
    Abstract: There is provided a single step procedure for the manufacture of 1-(alkoxymethyl)pyrrole compounds by reacting the appropriate pyrrole precursor with a dihalomethane reagent in the presence of an alkali metal alkoxide. The 1-(alkoxymethyl)pyrrole compounds are useful as molluscicidal, insecticidal, acaricidal and nematocidal agents.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: September 29, 1992
    Assignee: American Cyanamid Company
    Inventors: Venkataraman Kameswaran, Jerry M. Barton
  • Patent number: 5145865
    Abstract: Phenylcarboxylic acid derivatives having a hetero ring in the substituent of the formula: ##STR1## wherein R.sup.1 is halogen, alkyl, cycloalkyl, hydroxy, alkoxy, phenoxy which has a substituent selected from halogen and alkyl, carboxyl, alkylsulfonyloxy, phenylsulfonyloxy optionally substituted by halogen, alkylsulfonyloxyalkoxy, amino, alkanoylamino, benzoylamino, alkenyloxy, phenylalkoxyalkoxy, hydroxyalkoxy, phenylalkoxy having optionally 1 to 3 substituents selected from halogen, alkyl and alkoxy, halogenoalkyl, cycloalkyloxy optionally substituted by hydroxy, alkoxy substituted by cycloalkyl having optionally hydroxy substituent, imidazolylalkyl or imidazolylalkoxy; k is 0 or 1 to 3; or (R.sup.1).sub.k is alkylenedioxy; A is alkylene or alkylenoxy; l is 0 or 1; B is methylene or carbonyl; m is 0 or 1; D is alkylene; E is alkylene or alkenylene; n is 0 or 1; and R.sup.
    Type: Grant
    Filed: April 19, 1990
    Date of Patent: September 8, 1992
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Setsuro Fujii, deceased, by Shinichiro Fujii, administrator, by Kaoruko Takada, administrator, Hiroyuki Kawamura, Shinichi Watanabe
  • Patent number: 5142066
    Abstract: A stereoselective process for the preparation of the compounds of formula ##STR1## wherein R, R.sub.1, R.sub.2, a and b have the meanings reported in the specification, is described.The compounds of formula I have a remarkable central analgesic activity and they are useful in the pharmaceutical field.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: August 25, 1992
    Assignee: Zambon Group S.p.A
    Inventors: Mauro Napoletano, Gian C. Grancini, Carlo Veneziani, Dario Chiarino
  • Patent number: 5118704
    Abstract: Optically active or racemic compounds are provided having the formula ##STR1## where R.sub.2, R.sub.3, R.sub.4 and R.sub.6 are defined in the specification; R.sub.1 is selected from the group consisting of ##STR2## wherein Y is selected from the group consisting of hydroxy, nitro, cyano, azido, amino, acylamino, carboxyamido, trifluoromethyl, sulfate, sulfonamido, halogen, hydrocarbyl and hetero atom-substituted hydrocarbyl radicals, wherein said heteroatoms are selected from the group consisting of halogen, nitrogen, oxygen, sulfur and phosphorus and said hydrocarbyl radicals comprise from 1 to 12, preferably 1 to 6, carbon atoms, and a is an integer of from zero to 3, for instance zero to 2; and pharmaceutically acceptable salts thereof; as dopaminergics.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: June 2, 1992
    Assignee: Whitby Research, Inc.
    Inventors: Gevork Minaskanian, James V. Peck
  • Patent number: 5114466
    Abstract: 1-(3-Substituted benzyl)-3-halogeno-4-(1-halogenoalkyl)-2-pyrrolidinones of the general formula (I): ##STR1## where X represents a hydrogen atom or halogen atom, Y and Z each represents a chlorine atom or bromine atom, and R represents an alkyl group with 2 to 4 carbon atoms, are herbicides useful in rice paddy fields to control weeds therein, especially Echinochloa crusgalli and can be produced subjecting the corresponding 3-dihalogeno compounds to dehalogenation to remove one of the halogen atoms or by cyclizing a 2,2-dihalogenoacetamide derivative represented by the general formula (II) under the presence of an appropriate catalyst; ##STR2## in which X, Y, Z and R respectively have the same meanings as described above.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: May 19, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Kengo Oda, Koichi Moriyasu, Masao Hayashi, Makoto Nishida, Masami Oyamada, Akie Fujiwara, Junko Watanabe
  • Patent number: 5103007
    Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5101044
    Abstract: A process for the preparation of N-substituted pyrrolidin-2-ones of the general formula I ##STR1## where R.sup.1 is C.sub.1 - to C.sub.20 -alkyl, C.sub.6 - to C.sub.10 aryl or C.sub.7 - to C.sub.12 -aralkyl comprises hydrogenolytically cleaving 5-iminopyrrolidin-2-ones of the general formula II ##STR2## in which the R.sup.1 radicals are identical or different C.sub.1 - to C.sub.20 -alkyl, C.sub.6 - to C.sub.10 -aryl or C.sub.7 - to C.sub.12 -aralkyl, at super-atmospheric pressure and elevated temperature in the presence of a hydrogenation catalyst to give the pyrrolidin-2-ones I; specifically, the 5-iminopyrrolidin-2-ones of the formula II are obtained by reacting .beta.-cyanopropionic acid esters of the general formula III ##STR3## where R.sup.2 is C.sub.1 - to C.sub.20 -alkyl, C.sub.7 - to C.sub.12 -aralkyl or C.sub.6 - to C.sub.10 -aryl, with an amine of the general formula IVR.sup.1 --NH.sub.2 IVwhere R.sup.1 is as defined above.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Ludwig Schuster, Ulrich Koehler
  • Patent number: 5095121
    Abstract: 1S,4S and 1R,4R-2-Alkyl-2,5-diazabicyclo[2.2.1]heptanes useful as intermediates in the synthesis of certain antibacterial quinolones, are prepared respectively, from trans-4-hydroxy-L-proline and trans-4-hydroxy-D-proline via multistep procedures.
    Type: Grant
    Filed: January 8, 1991
    Date of Patent: March 10, 1992
    Assignee: Pfizer Inc
    Inventors: Tamim F. Braish, Darrell E. Fox
  • Patent number: 5095119
    Abstract: A compound of the formula: ##STR1## wherein A is ##STR2## in which X is .dbd.CH-- or .dbd.N--; R.sup.2 is hydrogen, alkyl, phenyl, benzyl or phenethyl; Y is --CH.sub.2--, --NH-- or --O--; and Z is --H.sub.2 or .dbd.O; B is His, Leu, Ile, Nva, Nle, Ala or Val; and R.sup.1 is hydrogen, alkyl, phenyl or phenylalkyl; or a pharmaceutically acceptable salt thereof are renin inhibitors.
    Type: Grant
    Filed: November 16, 1990
    Date of Patent: March 10, 1992
    Assignee: American Home Products Corporation
    Inventors: Timothy D. Ocain, David D. Deininger
  • Patent number: 5089518
    Abstract: This disclosure describes novel 3 or 4 substituted oxotremorine derivatives having polar substituted oxygen or sulfur groups. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and processes for the production of the compounds.
    Type: Grant
    Filed: August 22, 1990
    Date of Patent: February 18, 1992
    Assignee: American Cyanamid Company
    Inventors: Eugene J. Trybulski, Richard H. Kramss, Herbert J. Brabander
  • Patent number: 5081245
    Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5077427
    Abstract: A process for preparing .alpha.-formylamino nitriles of the formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or unsubstituted or substituted, with substituents which are inert under the reaction conditions, aliphatic or heteroaliphatic radicals with 1 to 10, cycloaliphatic or heterocycloaliphatic radicals with 3 to 6, araliphatic radicals with 7 to 12, heteroaraliphatic radicals with 4 to 12, aromatic radicals with 6 to 10 or heteroaromatic radicals with 3 to 10 carbon atoms, by reacting cyanohydrins of the formula II ##STR2## with the formamide III ##STR3## in the presence of acids, entails adding at least one ammonium salt to the reaction mixture.
    Type: Grant
    Filed: December 13, 1990
    Date of Patent: December 31, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fikentscher, Michael Kroener
  • Patent number: 5077426
    Abstract: A process for preparing .alpha.-formylamino nitriles of the formula Ia ##STR1## and Ib ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and each is hydrogen or unsubstituted or substituted, with substituents which are inert under the reaction conditions, aliphatic or heteroaliphatic radicals with 1 to 10, cycloaliphatic or heterocycloaliphatic radicals with 3 to 6, araliphatic radicals with 7 to 12, heteroaraliphatic radicals with 4 to 12, aromatic radicals with 6 to 10 or heteroarometic radicals with 3 to 10 carbon atoms, with the priviso that at least one of R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 is hydrogen, comprises reacting an iminodiacetonitrile of the formula II ##STR3## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meanings, with formamide of the formula III ##STR4## in the presence of formic acid or with a compound which provides formic acid, in the presence of acids.
    Type: Grant
    Filed: December 13, 1990
    Date of Patent: December 31, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fikentscher, Michael Kroener
  • Patent number: 5075302
    Abstract: Mercaptoacyl aminolactam inhibitors of endopeptidases of the formula ##STR1## wherein Y is -(CHR.sup.5).sub.n (CR.sup.3 R.sup.4)- or -(CR.sup.3 R.sup.4).sub.p X(CR.sup.3 R.sup.4).sub.q -,wherein two substituents selected from the group consisting of R.sup.3, R.sup.4 and R.sup.5, can form a benzene, cyclopentane or cyclohexane ring;X is -O-, -S-, -SO- or -SO.sub.2 -;Q is hydrogen or R.sup.6 CO-;m is 1 or 2;n is 1, 2, 3 or 4;p is 1 or 2;q is 2 or 3;R.sup.1 is lower alkyl, aryl or heteroaryl;R.sup.2 is hydrogen, lower alkyl, hydroxylower alkyl, lower alkoxylower alkyl, aryllower alkyl or heteroaryllower alkyl;R.sup.3 and R.sup.4 are independently hydrogen, lower alkyl, aryllower alkyl or heteroaryllower alkyl;R.sup.5 is hydrogen, lower alkyl, aryllower alkyl, heteroaryllower alkyl, hydroxy, lower alkoxy, mercapto, or lower alkylthio; and R.sup.
    Type: Grant
    Filed: March 9, 1990
    Date of Patent: December 24, 1991
    Assignee: Schering Corporation
    Inventor: Bernard R. Neustadt
  • Patent number: 5061725
    Abstract: (Pyrrolidin-2-one-1-yl)acetamides of general formula (I) ##STR1## wherein R is hydrogen or hydroxyl, R.sub.1 is hydrogen, R.sub.2 is selected from the group consisting of:2-aminoethyl,2-(N,N-diisopropyl) aminoethyl,3-(pyrrolidin-2-one-1-yl) propyl,2-[N-(pyrrolidin-2-one-1-yl) acetyl] aminoethyl,2-hydroxyethyl,(glycerophosphorylethanolamino) carbonylmethyl,1-trimethylammonium-3-carboxy-2-propyloxy-carbonylmethyl chloride,(prolinol-1-yl) carbonylmethyl,1-trimethylammonium-3-carboxyisopropyl), and3-pyridylcarbamide;or R.sub.1 and R.sub.2 taken together, are such as to form a cycle of formula ##STR2## wherein R.sub.3 is selected from the group consisting of phenyl substituted with halogens or halogen-substituted lower (C.sub.1 -C.sub.4) alkyls and 4-morpholinocarbonylmethyl 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 (I).
    Type: Grant
    Filed: July 12, 1990
    Date of Patent: October 29, 1991
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Fabio Giannessi, Orlando Ghirardi, Domenico Misiti, Maria O. Tinti, Carlo Sclolastico
  • Patent number: 5061804
    Abstract: 3-thio pyrrolidines are intermediates for carbapenams.
    Type: Grant
    Filed: March 6, 1990
    Date of Patent: October 29, 1991
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masayoshi Murata, Hideo Tsutsumi, Keiji Matsuda, Hohji Hattori, Takashi Nakajima
  • 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: 5049680
    Abstract: The present invention deals with novel quaternary polymeric compounds and their application as softening, anti-tangle, and conditioning agents. The polymers conform to the following structure: ##STR1## R is selected from CH.sub.3 --(CH.sub.2).sub.b --; CH3--(CH2).sub.c --(CH.dbd.CH)--(CH.sub.2).sub.d ;CH.sub.3 --(CH.sub.2).sub.e --CH(CH.sub.3)--(CH.sub.2).sub.f --;CH.sub.3 --(CH.sub.2).sub.b --O--R.sup.1 --(CH.sub.2).sub.3 --;CH.sub.3 --(CH.sub.2).sub.d --CH(CH.sub.3)--(CH.sub.2).sub.e --O--R.sup.1 --(CH.sub.2).sub.3 -- and ##STR2## R.sup.1 is--(CH.sub.2 CH.sub.2 --O).sub.x --(CH.sub.2 CH(CH.sub.3)--O).sub.y --(CH.sub.2 CH.sub.2 O).sub.z --;x y and z are independently integers from 0 to 20;b,c,d,e are independently integers from 5 to 20;m and n are independently integers from 4 to 20;a is an integer from 2 to 2,000;Y is an anionic counter ion needed for charge balance and is selected from chloride, bromide, sulfate, and phosphate.
    Type: Grant
    Filed: May 3, 1990
    Date of Patent: September 17, 1991
    Assignee: LCE Partnership
    Inventor: Anthony J. O'Lenick, Jr.
  • Patent number: 5047570
    Abstract: 3-Amino-2-cyanoacrylonitrile derivatives of the formula ##STR1## where R is substituted C.sub.1 -C.sub.10 -alkyl, substituted or unsubstituted styryl, substituted or unsubstituted phenyl or aromatic heterocyclyl, are prepared by treating a nitrile in an inert organic diluent at from 0.degree. to +30.degree. C. with a substituted or unsubstituted C.sub.1 -C.sub.6 -alkanol in the presence of a hydrogen halide and reacting the resulting iminoester hydrohalide directly or after isolation with malodinitrile in an inert organic diluent at from 20.degree. to 100.degree. C. in the presence of a base.
    Type: Grant
    Filed: February 10, 1989
    Date of Patent: September 10, 1991
    Assignee: BASF Aktiengesellschaft
    Inventor: Ernst Schefczik
  • Patent number: 5041535
    Abstract: The new peptides of the Formulae(1) Glp-Lys-NH.sub.2(2) Glp-Glu-Lys-NH.sub.2(3) Arg-Lys-Glu-NH.sub.2(4) Arg-lys-Asp-NH.sub.2(5) Arg-Lys-Glu-OH(6) Arg-Lys-Gln-OH(7) Leu-Val-Ala-OH(8) Arg-Orn-Asp-Val-NH.sub.2(9) Arg-Orn-Asp-Val-OH(10) Lys-Glu-Lys-Lys-OH(11) Lys-Leu-Lys-Lys-OH(12) Lys-Asp-Leu-Lys-OH(13) Glu-Leu-Val-Ala-OH and(14) Leu-Pro-Ala-Gly-OHand acid addition salts thereof inhibit the proliferation of leukaemic cells and exhibit immunostimulant effect.
    Type: Grant
    Filed: November 20, 1987
    Date of Patent: August 20, 1991
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt.
    Inventors: Olga Nyeki nee Kuprina, Istvan Schon, Lajos Kisfaludy, Laszlo Denes, Gyorgy Hajos, Laszlo Szporny, Bela Szende, Karoly Lapis
  • Patent number: 5026861
    Abstract: Novel cyclic vinylogous N-hydroxy-N-methylureas are useful in the treatment of leukotriene mediated conditions such as asthma and rheumatoid arthritis.
    Type: Grant
    Filed: July 17, 1989
    Date of Patent: June 25, 1991
    Assignee: Merrell Dow Pharmaceuticals
    Inventors: Gary A. Flynn, Douglas W. Beight
  • Patent number: 5023338
    Abstract: A compound of the formula: ##STR1## wherein A is ##STR2## in which X is .dbd.CH-- or .dbd.N--; R.sup.2 is hydrogen, alky, phenyl, benzyl or phenethyl; Y is --CH.sub.2 --, --NH-- or --O--; and Z is --H.sub.2 or .dbd.O; B is His, Leu, Ile, Nva, Nle, Ala or Val; and R.sup.1 is hydrogen, alkyl, phenyl or phenylalkyl; or a pharmaceutically acceptable salt thereof are renin inhibitors.
    Type: Grant
    Filed: March 8, 1990
    Date of Patent: June 11, 1991
    Assignee: American Home Products Corporation
    Inventors: Timothy D. Ocain, David D. Deininger
  • 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: 5011941
    Abstract: The invention relates primarily to quaternized compounds having the formula ##STR1## wherein n and n' are each independently integers having a value of from 1 to 25; p is an integer having a value of from 1 to 4; Y and Y' are each independently H or CH.sub.3 ; R is linear alkyl, alkenyl, or amidoalkyl having from 8 to 22 carbon atoms and is optionally substituted with C.sub.1 to C.sub.4 alkyl; Z is linear alkylene having from 3 to 8 carbon atoms and is optionally substituted with lower alkyl and A.sup.- is an anion.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: April 30, 1991
    Assignee: GAF Chemicals Corporation
    Inventors: Ratan K. Chaudhuri, David J. Tracy, Robert B. Login
  • Patent number: 5008104
    Abstract: The invention relates primarily to quaternized compounds having the formula ##STR1## wherein n and n' are each independently integers having a value of from 1 to 25; p is an integer having a value of from 1 to 4; Y and Y' are each independently H or CH.sub.3 ; R is linear alkyl, alkenyl, or amidoalkyl having from 8 to 22 carbon atoms and is optionally substituted with C.sub.1 to C.sub.4 alkyl; Z is linear alkylene having from 3 to 8 carbon atoms and is optionally substituted with lower alkyl and A.sup.- is an anion.
    Type: Grant
    Filed: June 22, 1989
    Date of Patent: April 16, 1991
    Assignee: GAF Chemicals Corporation
    Inventors: Ratan K. Chaudhuri, David J. Tracy, Robert B. Login
  • Patent number: 5006511
    Abstract: Enzyme di- or tripeptides of the formula: ##STR1## and analogs thereof which inhibit renin and are useful for treating various forms of renin-associated hypertension, hyperaldosteronism and congestive heart failure; compositions containing these renin-inhibitory peptides, optionally with other antihypertensive agents; and methods of treating hypertension, hyperaldosteronism or congestive heart failure or of establishing renin as a causative factor in these problems which employ these novel peptides.
    Type: Grant
    Filed: August 26, 1988
    Date of Patent: April 9, 1991
    Assignee: Merck & Co., Inc.
    Inventors: William J. Greenlee, Daniel F. Veber, Peter D. Williams
  • Patent number: 5006157
    Abstract: A cyclic amide compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, a haloalkoxy group, a lower alkylthio group or a nitro group; Y is a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a phenyl group, an alkoxy group, a cycloalkoxy group, a cycloalkylalkoxy group, an alkenyloxy group, an alkynyloxy group, a benzyloxy group, a phenoxy group, a haloalkoxy group, a lower alkoxy-lower alkoxy group, a cyanoalkoxy group, an alkylthio group, an alkenylthio group, an alkynylthio group, a benzylthio group, a phenylthio group, ##STR2## (wherein W is an oxygen atom or a sulfur atom, R.sup.3 is a hydrogen atom or an alkyl group and R.sup.4 is an alkyl group), ##STR3## (wherein each of R.sup.5 and R.sup.6 is a hydrogen atom or a lower alkyl group, an alkylsulfonyl group, ##STR4## (wherein R.sup.5 and R.sup.
    Type: Grant
    Filed: November 28, 1989
    Date of Patent: April 9, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuyuki Ohba, Atsuhiko Ikeda, Kenji Matsunari, Yuji Yamada, Michiya Hirata, Yasuo Nakamura, Akira Takeuchi, Hiroyuki Karino
  • Patent number: 4962198
    Abstract: The invention relates to a generally applicable process for the hydroxylation of electrophilic aromatic compounds, according to which the electrophilic aromatic compounds are reacted with organic hydroperoxides in the presence of bases.
    Type: Grant
    Filed: July 7, 1989
    Date of Patent: October 9, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Mieczyslaw Makosza, Krzysztof Sienkiewicz
  • Patent number: 4962204
    Abstract: .alpha.-Pyrrolidones and cyclic amidines 1a and 1b, respectively, for washing gases ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.3 -C.sub.10 -cycloalkyl or C.sub.3 -C.sub.10 -cycloalkoxy or are bonded to one another to form a ring, R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, phenyl or naphthyl and R.sup.4 and R.sup.5 are each hydrogen or C.sub.1 -C.sub.4 -alkyl, are prepared by a method in which an amine II ##STR2## where R.sup.3' is hydrogen, tert-butyl, phenyl or naphthyl, is reacted with an .alpha.,.beta.-unsaturated carboxylic acid derivative III ##STR3## where X is OR', --NR'R", --NHR' or --NH.sub.2 and R' and R" are each C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl or phenyl, or with an .alpha.,.beta.-unsaturated nitrile IV ##STR4## in the presence of a free radical initiator, and, where R.sup.3' is hydrogen and it is intended to prepare a compound in which R.sup.3' is C.sub.1 -C.sub.
    Type: Grant
    Filed: April 25, 1989
    Date of Patent: October 9, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Ludwig Wambach
  • Patent number: 4960788
    Abstract: Compounds of formula ##STR1## (wherein R, R.sub.1, R.sub.2, R.sub.3 and n have the meanings reported in the specification), their salts with pharmaceutically acceptable acids, process for their preparation and pharmaceutical compositions containing them are described.The compounds of formula I have a remarkable analgesic activity.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: October 2, 1990
    Assignee: Zambon Group S.p.A.
    Inventors: Angelo Carenzi, Dario Chiarino, Davide Della Bella, Gian Carlo Grancini, Carlo Veneziani
  • Patent number: 4960457
    Abstract: Substituted 1,3-diphenyl pyrrolidones of the formula ##STR1## in which R.sup.1 and R.sup.3 are halogen, trifluoromethyl, cyano, alkyl or alkoxy, R.sup.2 is H or halogen, and R.sup.4 is alkyl or haloalkyl, are useful as herbicidal agents.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: October 2, 1990
    Assignee: ICI Americas Inc.
    Inventor: Frank X. Woolard
  • Patent number: 4956003
    Abstract: Cyclohexane-1,3-dione derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meanings given in the disclosure, and the use thereof for combating unwanted plants, especially Gramineae.
    Type: Grant
    Filed: March 27, 1989
    Date of Patent: September 11, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Jahn, Rainer Becker, Norbert Goetz, Bruno Wuerzer
  • Patent number: 4943639
    Abstract: (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide, its preparation and pharmaceutical compositions containing the same. It can be prepared either by reacting (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid successively with an alkyl haloformate and with ammonia, or, by cyclizing an (S)-2-amino-butanamide of the formula X--CH.sub.2 CH.sub.2 --Y--NHCH(C.sub.2 H.sub.5)CONH.sub.2 wherein Y is a --CH.sub.2 -- radical when X represents a ZOOC-- radical and Y is a --CO-- radical when X represents a HalCH.sub.2 -- radical, Z being a C.sub.1 -C.sub.4 alkyl radical and Hal a halogen atom.This laevorotatory enantiomer has been found to have significantly higher protective activity against hypoxia and ischemia than the corresponding racemate.
    Type: Grant
    Filed: February 16, 1989
    Date of Patent: July 24, 1990
    Assignee: U C B Societe Anonyme
    Inventors: Jean Gobert, Jean-Pierre Geerts, Guy Bodson
  • Patent number: 4924006
    Abstract: What is provided herein are new and useful N-pyrrolidonyl alkyl amino 1,3,4-butanetriol compounds having the formula: ##STR1## where X is alkylene C.sub.1 -C.sub.5, andn is 1-4.
    Type: Grant
    Filed: October 2, 1989
    Date of Patent: May 8, 1990
    Assignee: GAF Chemical Corporation
    Inventors: Lowell R. Anderson, Mohamed M. Hashem, Robert B. Login
  • Patent number: 4918198
    Abstract: This invention provides novel and useful surfactants having the formula: ##STR1## where R is a long chain fatty acid alkyl group, saturated or unsaturated, e.g. having from 8-22 carbon atoms, as for example, lauryl, stearyl, oleyl, palmityl, myristyl, and mixtures such as coco, tallow, etc.,M is a metal ion, preferably an alkali metal such as sodium, potassium, etc., andn is 1-6.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: April 17, 1990
    Assignee: GAF Chemicals Corporation
    Inventors: Lowell R. Anderson, Mohamed M. Hashem, Robert B. Login
  • Patent number: 4902710
    Abstract: The present invention provides propanamines, substituted at the 3-position of the propanamine chain with a thio, sulfinyl or sulfonyl moiety, which are capable of selectively inhibiting the uptake of serotonin and norepinephrine.
    Type: Grant
    Filed: December 14, 1988
    Date of Patent: February 20, 1990
    Assignee: Eli Lilly and Company
    Inventors: Bennie J. Foster, David C. Hunden, Edward R. Lavagnino
  • 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: 4886911
    Abstract: The invention concerns compounds of formula I ##STR1## wherein: X and Y are independently selected from the group consisting of hydrogen, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, and the group wherein X and Y together from a three or four-membered carbon bridge the bridge optionally comprising one or both of a double bond and a carbonyl group;Z is selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.4 alkyl and C.sub.1 to C.sub.4 alkanoyl;R.sup.1 is selected from the group consisting of: hydrogen; an acyl group; and an inorganic or organic cation;R.sup.2 is selected from the group consisting of: C.sub.1 to c.sub.6 alkyl; C.sub.2 to C.sub.6 alkenyl; C.sub.2 to C.sub.6 haloakenyl; C.sub.2 to C.sub.6 alkynyl; and substituted C.sub.1 to C.sub.
    Type: Grant
    Filed: June 12, 1987
    Date of Patent: December 12, 1989
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Craig G. Lovel
  • Patent number: 4885158
    Abstract: The invention relates primarily to quaternized compounds having the formula ##STR1## wherein m is an integer having a value of from 1 to 4; R is alkylene having from 3 to 8 carbon atoms and is optionally substituted with C.sub.1 to C.sub.4 alkyl; R.sub.1, R.sub.2 and R.sub.3 are each independently selected from the group of alkyl, alkyloxyalkyl, alkyloxyalkenyl, hydroxyalkyl, aryl, aralkyl, alkaryl, alkyl amidoalkyl, alkyl carbamoylalkyl, aryl amido alkyl and aryl carbamoyalkyl radicals, and R.sub.2 and R.sub.3, together with the quaternized nitrogen atom can form a heterocyclic radical containing from 1 to 2 heteroatoms selected from the group of nitrogen, sulfur and oxygen, in which case R.sub.1 can represent a double bond in the heterocyclic structure or can be any of the aforementioned groups for R.sub.1, R.sub.2 and R.sub.3 ; said groups R.sub.1, R.sub.2 and R.sub.3 each having from 1 to 30 carbon atoms and at least one of R.sub.1, R.sub.2 and R.sub.3 is a radical having from 8 to 30 carbon atoms when R.
    Type: Grant
    Filed: April 29, 1988
    Date of Patent: December 5, 1989
    Assignee: GAF Corporation
    Inventors: David J. Tracy, Thomas Rizzo, Robert B. Login
  • Patent number: 4876360
    Abstract: A novel compound, namely, 1-thiocarbamylmethylpyrrolidine-2-thione has the following formula: ##STR1## A process for preparing said compound comprises reacting a derivative of pyrrolidone-2 of the general formula: ##STR2## wherein R is nitrile or carbamoyl, with phosphorus pentasulphide in an inert non-polar solvent at a temperature above room temperature, followed by treatment of the resulting precipitate with water upon boiling and isolation of the desired product.The compound according to the present invention exhibits antihypoxic and nootropic activity.
    Type: Grant
    Filed: April 5, 1989
    Date of Patent: October 24, 1989
    Inventors: Vladimir G. Granik, Tatyana V. Stezhko, Robert G. Glushkov, Mikhail D. Mashkovsky, Lidia F. Roschina, Antonina I. Polezhaeva, Roza B. Parimbetova, Jury G. Bobkov, Alexandr S. Losev, Irina A. Ivanova
  • Patent number: 4874422
    Abstract: 1-Phenyl-3-carboxyamidopyrrolidones of the formula ##STR1## in which R.sup.1 is H, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, phenyl, halophenyl, benzyl, halobenzyl, or alkyl substituted with alkoxy, alkyltyhio, phenyl, hydroxy or cyano; and R.sup.2 is H or alkyl; or R.sup.1 and R.sup.2 are combined as alkylene or alkyleneoxyalkylene; R.sup.3 is alkyl or alkenyl; R.sup.4 is H, halogen, CH.sub.3, CF.sub.3, CF.sub.2 CHF.sub.2, OCF.sub.2 CHF.sub.2, OCHF.sub.2, OCF.sub.3, SCH.sub.3, S(O)CH.sub.3, SO.sub.2 CH.sub.3, methoxyiminomethyl, methoxyimino-1-ethyl, benzyloxyiminomethyl, or benzyloxyimino-1-ethyl;n is zero or 1; X is H or halogen; Y is O or S; and Z is O or S, are useful as herbicidal agents.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: October 17, 1989
    Assignee: ICI Americas Inc.
    Inventor: Frank X. Woolard
  • Patent number: 4864017
    Abstract: The present invention provides novel renin-inhibiting peptides of the formula X-A.sub.6 -B.sub.7 -C.sub.8 -D.sub.9 -E.sub.10 -F.sub.11 -G.sub.12 -H.sub.13 - I.sub.14 -Z, wherein the E.sub.10 -F.sub.11 moiety is a dihydroxyethylene isostere, X and Z are terminal groups, and the remaining variables are absent or are amino acid residues. Such inhibitors are useful for the control of hypertension.
    Type: Grant
    Filed: August 23, 1988
    Date of Patent: September 5, 1989
    Assignee: The Upjohn Company
    Inventor: Suvit Thaisrivongs
  • Patent number: 4859206
    Abstract: This invention encompasses compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 independently are hydrogen, C.sub.1-4 alkyl, or C.sub.2-4 hydroxyalkyl; one of R.sup.3 to R.sup.7 is --SO.sub.3 H or --COOH; and the remaining of R.sup.3 to R.sup.7 independently are hydrogen, chlorine, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, or --NR.sup.8 R.sup.9, where R.sup.8 and R.sup.9 independently are hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkoxy, or where --NR.sup.8 R.sup.9 is piperidine, morpholine, piperazine, or pyrrolidone; or a water soluble salt thereof; hair dye preparation containing these compounds, and methods for dyeing hair using such preparation.
    Type: Grant
    Filed: February 26, 1988
    Date of Patent: August 22, 1989
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: David Rose, Edgar Lieske, Horst Hoeffkes, Norbert Maak
  • Patent number: 4859780
    Abstract: Hydrophilic modifier monomers of the formula [X-T].sub.z 'G are disclosed wherein X is a reactive group, G is a hydrophilic group and T is a divalent linking group, z' being a number up to the available valence of G, excess G valences being taken up by hydrogen. The monomers of the invention can be used to boost the hydrophilic nature of a wide variety of polymeric materials or be polymerized themselves with varying degrees of copolymerizable monomers. They are particularly suited for making hydrophilic contact lens materials.
    Type: Grant
    Filed: February 26, 1988
    Date of Patent: August 22, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Frank Molock, J. Richard Robertson, Jr., Kai C. Su
  • Patent number: 4845235
    Abstract: A pyrroline derivative represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 each independently stand for an alkyl (C.sub.1-6), allyl, alkoxy (C.sub.1-6) ethyl, allyloxyethyl, phenoxyethyl, phenylalkyl (C.sub.1-3), alkoxy (C.sub.1-6) carbonylalkyl (C.sub.1-3) or phenoxyethoxycarbonylalkyl (C.sub.2-3) group and R.sub.3 stands for a hydrogen atom or R.sub.3 ', wherein R.sub.3 ' stands for an alkyl (C.sub.1-6), allyl, benzyl, chlorobenzyl, nitrobenzyl, phenethyl, alkoxy (C.sub.1-6) carbonylalkyl (C.sub.1-3), phenoxyethoxycarbonylalkyl (C.sub.2-3) or cyanoalkyl (C.sub.1-2) group, a process for producing a pyrroline derivative represented by the formula (I) and methods for dyeing a hydrophobic fiber and coloring a synthetic resin with the same.
    Type: Grant
    Filed: May 15, 1987
    Date of Patent: July 4, 1989
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hiroyuki Matumoto, Hidenori Imai, Shozi Tada
  • Patent number: 4839380
    Abstract: A novel compound, namely, 1-thiocarbamylmethylpyrrolidine-2-thione has the following formula: ##STR1## A process for preparing said compound comprises reacting a derivative of pyrrolidone-2 of the general formula: ##STR2## wherein R is nitrile or carbamoyl, with phosphorus pentasulphide in an inert non-polar solvent at a temperature above room temperature, followed by treatment of the resulting precipitate with water upon boiling and isolation of the desired product.The compound according to the present invention exhibits antihypoxic and nootropic activity.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: June 13, 1989
    Inventors: Vladimir G. Granik, Tatyana V. Stezhko, Robert G. Glushkov, Mikhail D. Mashkovsky, Lidia F. Roschina, Antonina I. Polezhaeva, Roza B. Parimbetova, Jury G. Bobkov, Alexandr S. Losev, Irina A. Ivanova