Three Or More Amino Nitrogens Patents (Class 514/674)
  • Patent number: 5889061
    Abstract: Compounds of Formula I:E-NH-D-NH-B-A-B-NH-D-NH-E (I)wherein A is C.sub.2 -C.sub.6 alkene, C.sub.3 -C.sub.6 cycloalkyl, cycloalkenyl, or cycloaryl; B is independently a single bond, C.sub.1 -C.sub.6 alkyl alkenyl; D is independently C.sub.1 -C.sub.6 alkyl or alkenyl, or C.sub.3 -C.sub.6 cycloalkyl, cycloalkenyl, or cycloaryl; and E is independently H, C.sub.1 -C.sub.6 alkyl or alkenyl; and pharmaceutically-suitable salts thereof; a synthetic method therefor, pharmaceutical dosage forms containing one of more of these compounds, and use of these compounds in the treatment of neoplastic cell growth, are disclosed.
    Type: Grant
    Filed: October 15, 1997
    Date of Patent: March 30, 1999
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Benjamin J. Frydman, Laurence J. Marton, Vendohar K. Reddy, Aldonia L. Valasinas, Donald T. Witiak
  • Patent number: 5886051
    Abstract: Methods and pharmaceutical compositions in unit dosage form for treating neurodegeneration in a human or non-human animal afflicted therewith wherein the active agent is a therapeutically effective amount of a polyamine having the formula: ##STR1## or a salt thereof with a pharmaceutically acceptable acid wherein: R.sub.1 and R.sub.6 may be the same or different and are hydrogen, alkyl, hydrocarbyl aryl, hydrocarbyl aryl alkyl, cycloalkyl, or any of the foregoing wherein the alkyl chain is interrupted by at least one etheric oxygen atom;N.sup.1, N.sup.2, N.sup.3 and N.sup.4 are nitrogen atoms capable of protonation at physiological pH's;a and b may be the same or different and are integers from 1 to 4;A, B and C may be the same or different and are bridging groups of variable length.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: March 23, 1999
    Assignees: University Of Florida Research Foundation, Inc., SunPharm Corporation
    Inventors: Raymond J. Bergeron, Jr., Stefan Borg
  • Patent number: 5886050
    Abstract: Polyamines having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are alkyl, aralkyl or aryl having up to 10 carbon atoms; anda and b may be the same or different and are integers from 1 to 8; ora salt thereof with a pharmaceutically acceptable acid. Anti-neoplastic, anti-diarrheal, anti-peristaltic, gastro-intestinal anti-spasmodic, anti-viral, anti-retroviral, anti-psoriasis and insecticidal compositions comprising biologically effective amounts of the above-described amines and biologically acceptable carriers therefor are also disclosed, as well as methods of treatment, administration or application of biologically effective amounts of the polyamines of the invention. Also disclosed are methods for preparing the polyamines of the invention.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: March 23, 1999
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron, Jr.
  • Patent number: 5880161
    Abstract: Therapeutic polyamines useful as a cancer chemotherapeutic agents, including molecules having a formula R.sub.1 --NH--(CH.sub.2).sub.x --NH-- (CH.sub.2).sub.x --NH-- (CH.sub.2).sub.y --NH--(CH.sub.2).sub.z --NH--R, wherein R.sub.1 and R.sub.2 are hydrocarbon chains having 1 to 5 carbons and w, x, y and z are integer of 1 to 10, are disclosed. One such molecule is N.sup.1, N.sup.19 -bis(ethylamino)-5,10,15-triazanonadecane, which is longer than spermine. This preferred compound may be used alone or in combination with other therapeutic agents, such as 1,3-bis(2-chloroethyl)-1-nitrosourea or cis-Pt.
    Type: Grant
    Filed: July 29, 1996
    Date of Patent: March 9, 1999
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Hirak Subhra Basu, Burt Feuerstein, Keijiro Samejima, Laurence Marton
  • Patent number: 5866613
    Abstract: A polyamine and pharmaceutical composition containing an effective amount of the polyamine useful for administration to a human or non-human animal afflicted with neoplastic cells, the polyamine having the formula:R.sub.1 --NH--(CH.sub.2).sub.3 --NH--(CH.sub.2).sub.3 --NH--(CH.sub.2).sub.3 --NH--R.sub.2wherein R.sub.1 and R.sub.2 are both ethyl; or a salt thereof with a pharmaceutically acceptable acid, as well as a method of treatment comprising administering to such animals an effective amount of a polyamine of the above formula wherein R.sub.1 and R.sub.2 are each lower alkyl of 1-4 carbon atoms.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 2, 1999
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron
  • Patent number: 5827894
    Abstract: An anti-viral, anti-psoriasis or anti-retroviral therapy based on the administration of a compound having one of the formulae: ##STR1## wherein: R.sub.1 and R.sub.6 may be the same or different and are alkyl having from 1 to 12 carbon atoms or hydrocarbyl aralkyl having up to 12 carbon atoms;R.sub.2 -R.sub.5 may be the same or different and are H, R.sub.1 or R.sub.6 ;m is an integer from 3 to 6, inclusive;n is an integer from 3 to 6, inclusive; or(III) a salt thereof with a pharmaceutically acceptable acid.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: October 27, 1998
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron
  • Patent number: 5776352
    Abstract: The invention relates to a process for the treatment of water and of surfaces in contact with the said water in order to prevent the attachment and/or to, remove and/or to control macroorganisms, in particular molluscs, on the said surfaces in contact with the water, in which process at least one biocidal and/or biostatic active product is employed which is injected into the water and/or applied to the said surfaces, according to which process the active product(s) used comprise(s) at least one polyamine of formula I:R.sub.1 --NH?(CH.sub.2).sub.3 --NH!.sub.n --(CH.sub.2).sub.3 NH.sub.2(I)in which formula R.sub.1 is a C.sub.8 -C.sub.22 alkyl or alkenyl radical and/or at least one monoamine of formula II:R.sub.2 NH.sub.2 (II)in which formula R.sub.2 is a C.sub.8 -C.sub.22 alkyl or alkenyl radical, and n is an integer between 0 and 3 (inclusive).The invention also relates to a composition to be injected into the water and to a paint for covering the surfaces in contact with the water.
    Type: Grant
    Filed: April 1, 1996
    Date of Patent: July 7, 1998
    Inventor: Antoine Vanlaer
  • Patent number: 5760091
    Abstract: A preventive agent against adhesion of a marine organism comprising: at least one amine compound represented by the following formula (I): ##STR1## , wherein R is a C.sub.8-22 saturated or unsaturated aliphatic hydrocarbon group, R.sup.1 is hydrogen atom, aminopropyl, a C.sub.1-22 saturated aliphatic hydrocarbon or C.sub.2-22 unsaturated aliphatic hydrocarbon group, R.sup.2 is aminopropyl, a C.sub.1-8 saturated aliphatic hydrocarbon or C.sub.2-8 unsaturated aliphatic hydrocarbon group, provided that R.sup.1 is hydrogen atom or aminopropyl group when R.sup.2 is represents aminopropyl group, or a salt thereof; and at least one N-alkyl polyamine compound represented by the following formula (II):R--?NH(CH.sub.2).sub.3 !.sub.n --NH.sub.2 (II), wherein R is a C.sub.8-22 saturated or unsaturated aliphatic hydrocarbon group and n is an integer from 2 to 4, or a salt thereof in an amount of 0.1 to 9 parts by weight to one part by weight of the compound (I).
    Type: Grant
    Filed: March 20, 1996
    Date of Patent: June 2, 1998
    Assignee: Katayama Chemical, Inc.
    Inventors: Yoshiharu Wakao, Toru Yasunaga
  • Patent number: 5760092
    Abstract: Disclosed are allocolchinones, which are anti-mitotic agents. Allocolchinones bind to tubulin reversibly and are more effective at inhibiting microtubule formation than colchicine. 7-Acetamido-allocolchinone inhibits the growth of a number of tumor cell lines at concentrations about 100 times lower than colchicine. Also disclosed is a method of treating an individual with cancer by administering a composition which comprises a therapeutically effective amount of an allocolchinone which inhibits microtubule assembly. Administering a therapeutically effective amount of a composition which comprises an allocolchinone which inhibits microtubule assembly can also be used for treating inflammatory diseases, multiple sclerosis, primary biliary cirrhosis, Alzheimer's Disease and Behcet's Disease.
    Type: Grant
    Filed: March 11, 1996
    Date of Patent: June 2, 1998
    Assignee: Brandeis University
    Inventors: Serge M. Timasheff, Marina J. Gorbunoff, Bernardo Perez-Ramirez
  • Patent number: 5719193
    Abstract: This invention relates to a method of potentiating cell-mediated immunity which comprises administering to a patient a cell-mediated immunity potentiating amount of a compound of the formula:RHN--Z--NH--(CH.sub.2).sub.m --NH--Z--NHRor a pharmaceutically acceptable salt thereof, wherein m is an integer 3 to 12, Z is a saturated C.sub.2 -C.sub.6 alkylene moiety of straight or branched chain configuration, each R group is independently H, a C.sub.1 -C.sub.6 saturated or unsaturated hydrocarbyl, or --(CH.sub.2).sub.x --(Ar)--X wherein X is H, C.sub.1 -C.sub.6 alkoxy, halogen, C.sub.1 -C.sub.4 alkyl, or --S(O).sub.x R.sub.1, x is an integer 0, 1 or 2, and R.sub.1 is C.sub.1 -C.sub.6 alkyl.
    Type: Grant
    Filed: April 14, 1995
    Date of Patent: February 17, 1998
    Assignee: Merrell Pharmaceuticals, Inc.
    Inventors: Terry L. Bowlin, Nellikunja J. Prakash
  • Patent number: 5681837
    Abstract: A mosquito insecticidal composition for controlling the growth of mosquitos wherein the active agent is a polyamine having one of the formulae: ##STR1## wherein: R.sub.1 and R.sub.6 may be the same or different and are alkyl having from 1 to 12 carbon atoms or hydrocarbyl aralkyl having up to 12 carbon atoms;R.sub.2 -R.sub.5 may be the same or different and are H, R.sub.1 or R.sub.6 ;R.sub.7 is H, alkyl having from 1 to 12 carbon atoms, hydrocarbyl aryl or hydrocarbyl aralkyl, each having up to 12 carbon atoms;m is an integer from 3 to 6, inclusive;n is an integer from 3 to 6, inclusive; or(IV) a salt thereof with an acid and a carrier therefor.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: October 28, 1997
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron
  • Patent number: 5679682
    Abstract: A method of controlling the growth of mosquitos comprising administering to the mosquitos a mosquito insecticidal effective amount of a compound having one of the formulae: ##STR1##R.sub.1 --N.sup.1 H--(CH.sub.2).sub.3 --N.sup.2 H--(CH.sub.2).sub.3 --N.sup.3 H--(CH.sub.2).sub.4 --N.sup.4 H--(CH.sub.2).sub.3 --N.sup.5 H--(CH.sub.2).sub.3 --N.sup.6 H--R.sub.6 (II);or ##STR2## wherein: R.sub.1 and R.sub.6 may be the same or different and are alkyl having from 1 to 12 carbon atoms or hydrocarbyl aralkyl having up to 12 carbon atoms;R.sub.2 -R.sub.5 may be the same or different and are H, R.sub.1 or R.sub.6 ;R.sub.7 is H, alkyl having from 1 to 12 carbon atoms, hydrocarbyl aryl or hydrocarbyl aralkyl, each having up to 12 carbon atoms;m is an integer from 3 to 6, inclusive;n is an integer from 3 to 6, inclusive; or (IV) a salt thereof with an acid and a carrier therefor.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: October 21, 1997
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron
  • Patent number: 5677351
    Abstract: Polyamines having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are alkyl, aralkyl or aryl having up to 10 carbon atoms; anda and b may be the same or different and are integers from 1 to 8; or a salt thereof with a pharmaceutically acceptable acid. Anti-neoplastic, anti-diarrheal, anti-peristaltic, gastrointestinal anti-spasmodic, anti-viral, anti-retroviral, anti-psoriasis and insecticidal compositions comprising biologically effective amounts of the above-described amines and biologically acceptable carriers therefor are also disclosed, as well as methods of treatment, administration or application of biologically effective amounts of the polyamines of the invention. Also disclosed are methods for preparing the polyamines of the invention.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 14, 1997
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron, Jr.
  • Patent number: 5677352
    Abstract: Anti-diarrheal, anti-secretory, nitric oxide agonist, nitric oxide synthase activating or gastrointestinal anti-spasmodic compounds of the formula: ##STR1## wherein: R.sub.1 and R.sub.6 may be the same or different and are H, alkyl or aralkyl having from 1 to 12 carbon atoms;R.sub.2 -R.sub.5 may be the same or different and are H, R.sub.1 or R.sub.6 ;R.sub.7 is H, alkyl, aryl or aralkyl having from 1 to 12 carbon atoms;m is an integer from 3 to 6, inclusive; andn is an integer from 3 to 6, inclusive; or(IV) a salt thereof with a pharmaceutically acceptable acid; and a pharmaceutically acceptable carrier therefor. Methods of treatment utilizing the composition are also disclosed.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 14, 1997
    Assignee: University of Florida Research Foundation, Inc.
    Inventors: Raymond J. Bergeron, Jr., Charles A. Sninsky
  • Patent number: 5656671
    Abstract: Polyamines having the formula: ##STR1## wherein R.sup.1 and R.sub.2 are alkyl, aralkyl or aryl having up to 10 carbon atoms; anda and b may be the same or different and are integers from 1 to 8; ora salt thereof with a pharmaceutically acceptable acid. Anti-neoplastic, anti-diarrheal, anti-peristaltic, gastrointestinal anti-spasmodic, anti-viral, anti-retroviral, anti-psoriasis and insecticidal compositions comprising biologically effective amounts of the above-described amines and biologically acceptable carriers therefor are also disclosed, as well as methods of treatment, administration or application of biologically effective amounts of the polyamines of the invention. Also disclosed are methods for preparing the polyamines of the invention.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: August 12, 1997
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron, Jr.
  • Patent number: 5654287
    Abstract: The present invention relates to a method of treating a patient suffering from a neoplastic disease state comprising administering to said patient an effective antineoplastic amount of N,N'-bis[3-(ethylamino)propyl]-1,7-heptanediamine in conjunctive therapy with an effective antineoplastic amount of a cytotoxic agent selected from the group consisting of an antineoplastic vinca alkaloid, an antineoplastic antibiotic, an antineoplastic antimetabolite and an antineoplastic platinum coordination complex, wherein a synergistic antineoplastic effect results.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: August 5, 1997
    Assignee: Merrell Phamaceuticals Inc.
    Inventors: Nellikunja J. Prakash, Terry L. Bowlin
  • Patent number: 5646124
    Abstract: The present invention relates to a method of treating a patient suffering from a neoplastic disease state comprising administering to said patient an effective antineoplastic amount of N,N'-bis[3-(ethylamino)propyl]-1,7-heptanediamine in conjunctive therapy with an effective antineoplastic amount of a cytotoxic agent selected from the group consisting of an antineoplastic vinca alkaloid, an antineoplastic antibiotic, an antineoplastic antimetabolite and an antineoplastic platinum coordination complex, wherein a synergistic antineoplastic effect results.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: July 8, 1997
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Nellikunja J. Prakash, Terry L. Bowlin
  • Patent number: 5635218
    Abstract: The present invention relates to a method of treating a patient suffering from a neoplastic disease state comprising administering to said patient an effective antineoplastic amount of N,N'-bis[3-(ethylamino)propyl]-1,7-heptanediamine in conjunctive therapy with an effective antineoplastic amount of a cytotoxic agent selected from the group consisting of an antineoplastic vinca alkaloid, an antineoplastic antibiotic, an antineoplastic antimetabolite and an antineoplastic platinum coordination complex, wherein a synergistic antineoplastic effect results.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: June 3, 1997
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Nellikunja J. Prakash, Terry L. Bowlin
  • Patent number: 5627215
    Abstract: The invention relates to compounds of formula (I), R.sub.1 and R.sub.2, each independently of the other, are selected from lower alkyl that is unsubstituted or substituted by one or more fluorine atoms which are not linked to the carbon atom of R.sub.1 or R.sub.2 bonding the nitrogen; from lower alkenyl wherein the double bond does not originate from the carbon atom that is bonded to a nitrogen bonding R.sub.1 or R.sub.2 ; from lower alkynyl wherein the triple bond does not originate from the carbon atom that is bonded to a nitrogen bonding R.sub.1 or R.sub.2 ; from cycloalkyl; and from cycloalkyl-lower alkyl; with the proviso that not more than one of the two radicals R.sub.1 and R.sub.2 is methyl; or salts thereof. The mentioned compounds are pharmacologically active against disorders that are responsive to a recuction in intracellular polyamines, such as tumours or protozoal diseases.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: May 6, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Jorg Frei, Jaroslav Stanek
  • Patent number: 5622995
    Abstract: A method is provided for controlling the proliferation of molluscs in target habitat by applying to the habitat a compound or mixture of compounds which are amines, ethoxylated amines, quaternary amines, ethoxylated quaternary amines and cyclic amines.
    Type: Grant
    Filed: August 15, 1994
    Date of Patent: April 22, 1997
    Assignee: Electric Power Research Institute, Inc.
    Inventors: Billy D. Fellers, Arthur J. Freedman, Thomas M. Laronge
  • Patent number: 5614509
    Abstract: The use of NMDA receptor antagonists or their physiologically compatible salts for preventing the development of tolerance during the long-term treatment with benzodiazepine-receptor-binding active ingredients as well as the combination of new pharmaceutical agents with benzodiazepine-receptor-binding active ingredients is described.
    Type: Grant
    Filed: March 2, 1995
    Date of Patent: March 25, 1997
    Assignee: Schering Aktiengesellschaft
    Inventors: Lechoslaw Turski, Karin G. Steppuhn, Herbert Schneider, David N. Stephens
  • Patent number: 5565021
    Abstract: The invention relates to a process for the treatment of water and of surfaces in contact with the said water in order to prevent the attachment and/or to remove and/or to control macroorganisms, in particular molluscs, on the said surfaces in contact with the water, in which process at least one biocidal and/or biostatic active product is employed which is injected into the water and/or applied to the said surfaces, according to which process the active product(s) used comprise(s) at least one polyamine of formula I:R.sub.1 -NH[(CH.sub.2).sub.3 -NH].sub.n -(CH.sub.2).sub.3 NH.sub.2(I)in which formula R.sub.1 is a C.sub.8 -C.sub.22 alkyl or alkenyl radical and at least one monoamine of formula II:R.sub.2 NH.sub.2 (II)in which formula R.sub.2 is a C.sub.8-C.sub.22 alkyl or alkenyl radical, and n is an integer between 0 and 3 (inclusive).The invention also relates to a composition to be injected into the water and to a paint for covering the surfaces in contact with the water.
    Type: Grant
    Filed: December 28, 1994
    Date of Patent: October 15, 1996
    Inventor: Antoine Vanlaer
  • Patent number: 5561136
    Abstract: The present invention relates to a method of treating a patient suffering from a neoplastic disease state comprising administering to said patient an effective antineoplastic amount of N,N'-bis[3-(ethylamino)propyl]-1,7-heptanediamine in conjunctive therapy with an effective antineoplastic amount of a cytotoxic agent selected from the group consisting of an antineoplastic vinca alkaloid, an antineoplastic antibiotic, an antineoplastic antimetabolite and an antineoplastic platinum coordination complex, wherein a synergistic antineoplastic effect results.
    Type: Grant
    Filed: May 9, 1995
    Date of Patent: October 1, 1996
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Nellikunja J. Prakash, Terry L. Bowlin
  • Patent number: 5554656
    Abstract: The invention relates to a disinfectant concentrate which contains amine and alcohol wherein the alcohol component includes at least one glycol ether of limited miscibility with water and the amine component includes at least one secondary and/or tertiary alkyl amine free from hydroxyl groups. It also relates to a disinfectant producabile from the disinfectant concentrate, the use of the disinfectant concentrate and of the disinfectant as bactericide, in particular mycobactericide, fungicide or virucide.
    Type: Grant
    Filed: February 25, 1994
    Date of Patent: September 10, 1996
    Assignee: Reckitt & Colman Inc.
    Inventors: Bernd L ower, Heinz Eggensperger, Peter Goroncy-Bermes, Michael Mohr, Andreas Dettmann
  • Patent number: 5541230
    Abstract: Therapeutic polyamines useful as a cancer chemotherapeutic agents, including molecules having a formula R.sub.1 --NH--(CH.sub.2).sub.x --NH --(CH.sub.2).sub.x --NH--(CH.sub.2).sub.y --NH--(CH.sub.2).sub.z --NH--R, wherein R.sub.1 and R.sub.2 are hydrocarbon chains having 1 to 5 carbons and w, x, y and z are integers of 1 to 10, are disclosed. One such molecule is N.sup.1, N.sup.19 -bis(ethylamino)-5,10,15-triazanonadecane, which is longer than spermine. This preferred compound may be used alone or in combination with other therapeutic agents, such as 1,3-bis(2-chloroethyl)-1-nitrosourea or cis-Pt.
    Type: Grant
    Filed: November 5, 1993
    Date of Patent: July 30, 1996
    Inventors: Hirak S. Basu, Burt Feuerstein, Laurence Marton, Keijiro Samejima
  • Patent number: 5498522
    Abstract: Disclosed is a method that relates to the measurement of determinants related to the in-vivo induction of spermidine/spermine N.sup.1 -acetyltransferase (SSAT), subsequent to polyamine analog treatment (such as with a bis-ethyl spermine analog) of human malignant solid tumor types responsive to the polyamine analog. The method comprises the measurement of one or more SSAT-specific determinants that include SSAT enzyme activity, SSAT enzyme protein, and SSAT m-RNA transcripts. Alternatively, other determinants related to the SSAT induction may be measured. Such determinants include SSAT co-factor acetylCoenzyme A, and SSAT products N.sup.1 -acetylspermidine and N.sup.1 -acetylspermine. Measurements of these determinants may be useful as prognostic indicia and tumor response markers to evaluate the clinical effectiveness of anticancer agents comprising polyamine analogs.
    Type: Grant
    Filed: November 16, 1993
    Date of Patent: March 12, 1996
    Assignee: Health Research, Inc.
    Inventor: Carl W. Porter
  • Patent number: 5494935
    Abstract: Several new powerful chelating agents, suitable for the removal of a variety of certain heavy metal ions from the body of a mammal by oral application, have been synthesized and tested. Structurally, these compounds are partially lipophilic polyaminocarboxylic acids (PACA). They were synthesized in non-aqueous media from triethylenetetramine (TT) by monoalkylation of a primary amino group, followed by exhaustive carboxymethylation of the remaining amino groups using ethylbromoacetate and subsequent alkaline hydrolysis of the ester. In contrast to their non-lipophilic counterparts EDTA and DTPA, compositions of the present inventions exhibit appreciable absorption from the intestine and, therefore, can be administered orally. By varying the length of the alkyl chain, the chelons can be directed primarily to selected target organs. In addition, the compounds can be modified to target particular absorbed heavy metals.
    Type: Grant
    Filed: April 3, 1995
    Date of Patent: February 27, 1996
    Assignee: University of Utah Research Foundation
    Inventors: Scott C. Miller, Friedrich W. Bruenger
  • Patent number: 5462970
    Abstract: Anti-diarrheal, anti-secretory, nitric oxide agonist, nitric oxide synthase activating or gastrointestinal anti-spasmodic compounds of the formula: ##STR1## wherein: R.sub.1 and R.sub.6 may be the same or different and are H, alkyl or aralkyl having from 1 to 12 carbon atoms;R.sub.2 -R.sub.5 may be the same or different and are H, R.sub.1 or R.sub.6 ;R.sub.7 is H, alkyl, aryl or aralkyl having from 1 to 12 carbon atoms;m is an integer from 3 to 6, inclusive; andn is an integer from 3 to 6, inclusive; or(IV) a salt thereof with a pharmaceutically acceptable acid; and a pharmaceutically acceptable carrier therefor. Methods of treatment utilizing the composition are also disclosed.
    Type: Grant
    Filed: January 3, 1995
    Date of Patent: October 31, 1995
    Assignee: University of Florida Research Foundation, Inc.
    Inventors: Raymond J. Bergeron, Jr., Charles A. Sninsky
  • Patent number: 5455277
    Abstract: A mosquito insecticidal composition and method for controlling the growth of mosquitos employing a mosquito insecticidally effective amount of a compound having one of the formulae: ##STR1## wherein: R.sub.1 and R.sub.6 may be the same or different and are alkyl having from 1 to 12 carbon atoms or hydrocarbyl aralkyl having up to 12 carbon atoms;R.sub.2 -R.sub.5 may be the same or different and are H, R.sub.1 or R.sub.6 ;R.sub.7 is H, alkyl having from 1 to 12 carbon atoms, hydrocarbyl aryl or hydrocarbyl aralkyl each having up to 12 carbon atoms;m is an integer from 3 to 6, inclusive;n is an integer from 3 to 6, inclusive; or(IV) a salt thereof with an acid and a carrier therefor.
    Type: Grant
    Filed: December 8, 1993
    Date of Patent: October 3, 1995
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron
  • Patent number: 5451608
    Abstract: Derivatives of 2-amino-1,2,3,4-tetrahydronaphthalene and their use in therapeutic field are described.The compounds are particularly useful in the treatment of arterial hypertension, cardiac decompensation and renal failure, in the treatment of peripheral arteriopathies and in cerebrovascular insufficiency.
    Type: Grant
    Filed: July 28, 1994
    Date of Patent: September 19, 1995
    Assignee: Zambon Group S.p.A.
    Inventors: Francesco Santangelo, Giorgio Bertolini, Cesare Casagrande, Francesco Marchini, Stefania Montanari, Claudio Semeraro
  • Patent number: 5444093
    Abstract: Wood preservatives contain a copper salt, a polyamine and a fatty amine and are used for preserving wood from fungi and termites.
    Type: Grant
    Filed: November 3, 1993
    Date of Patent: August 22, 1995
    Assignee: Dr. Wolman GmbH
    Inventors: Reimer Goettsche, Hans-Volker Borck
  • Patent number: 5434145
    Abstract: The present invention relates to certain polyamine thiols which are useful as radioprotective agents.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: July 18, 1995
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Michael L. Edwards, Ronald D. Snyder
  • Patent number: 5432202
    Abstract: Methods for regulating cation transport across cellular membranes possessing cation channels are provided. The cell membrane possessing a specific ion channel is exposed to a non-aromatic polyamine compound having a lysine- or arginine-based moiety (or a guanidine moiety) coupled to a straight chain polyamine.These polyamines as well as a method for regulating NMDA through a spermidine-like effect on NMDA receptors by exposing a cell membrane to selected polyamines are also provided.
    Type: Grant
    Filed: June 9, 1993
    Date of Patent: July 11, 1995
    Assignee: New York University
    Inventors: Bruce D. Cherksey, Rodolfo R. Llinas, Mutsuyuki Sugimori
  • Patent number: 5403862
    Abstract: Several new powerful chelating agents, suitable for the removal of a variety of certain heavy metal ions from the body by oral application, have been synthesized and tested. Structurally, these compounds are partially lipophilic polyaminocarboxylic acids (PACA). They were synthesized in non-aqueous media from triethylenetetramine (TT) by monoalkylation of a primary amino group, followed by exhaustive carboxymethylation of the remaining amino groups using ethylbromoacetate and subsequent alkaline hydrolysis of the ester. Gel permeation chromatography of a mixture of the PACA and actinide elements have shown these substances to be strong chelating agents similar to EDTA or DTPA. In contrast to their non-lipophilic counterparts EDTA and DTPA, compositions of the present inventions exhibit appreciable absorption from the intestine and, therefore, can be administered orally. By varying the length of the alkyl chain, the chelons can be directed primarily to selected target organs.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: April 4, 1995
    Assignee: University of Utah Research Foundation
    Inventors: Scott C. Miller, Friedrich W. Bruenger
  • Patent number: 5399570
    Abstract: Aspartic acid derivatives of the formula ##STR1## in which X denotes, for example, ##STR2## and R denotes, for example, cyclohexylamino, have useful pharmacological properties.
    Type: Grant
    Filed: March 25, 1993
    Date of Patent: March 21, 1995
    Assignee: Cassella Aktiengesellschaft
    Inventors: Otmar Klingler, Gerhard Zoller, Melitta Just, Bernd Jablonka
  • Patent number: 5393789
    Abstract: The invention relates to a disinfectant concentrate which includes amine and alcohol and is characterized in that the alcohol component includes at least one aromatic alcohol and the amine component includes at least one tertiary alkyl amine which is free of hydroxyl groups. It is also relates to a disinfectant which is preparable from the disinfectant concentrate, and to the use of the disinfectant concentrate or disinfectant as a bactericide, in particular a Mycobactericide, fungicide or virucide.
    Type: Grant
    Filed: January 29, 1993
    Date of Patent: February 28, 1995
    Assignee: Eastman Kodak Company
    Inventors: Heinz Eggensperger, Lower Bernd, Michael Mohr, Peter Goroncy-Bermes, Wolfgang Beilfuss
  • Patent number: 5322856
    Abstract: A fortified glutaraldehyde compound with and without dual synergistic phenols is provided for disinfection and sanitization. One formula consists of: glutaraldehyde; dual quaternary ammonium chloride (n-alkyl dimethylethylbenzyl ammonium chloride and n-alkyl dimethylbenzyl ammonium chloride); para tertiary amyl phenol; ortho phenyl phenol; citric or acetic acid; sodium citrate; isopropyl or ethyl alcohol; triethanol amine-HCl; and water in the following proportions: 25.00 to 42.00 grams; 25.00 grams; 1.00 gram; 1.00 gram; 0.50 grams; 0.25 grams; 14.00 grams; 1.00 gram; and 32.25 to 15.25 grams. The formula for environmentally protected uses consists of: glutaraldehyde; dual quaternary ammonium chloride (n-alkyl dimethylethylbenzyl ammonium chloride and n-alkyl dimethylbenzyl ammonium chloride); citric or acetic acid; sodium citrate; isopropyl or ethyl alcohol; triethanol amine-HCl; and water in the following proportions: 25.00 to 42.00 grams; 25.00 grams; 0.50 grams; 0.25 grams; 14.00 grams; 1.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: June 21, 1994
    Inventor: Howard Martin
  • Patent number: 5276047
    Abstract: The invention relates to a liquid preparation containing 1,2-benzoisothiazoline-3-one (BIT) and amines and optionally containing additional solvents and common additives, and containing as amine one or more amines having the general formula ##STR1## wherein R represents a straight-chained or branched alkyl or alkylene radical having 10 to 14 C atoms; n+m has a value of 4 to 12 and neither n nor m can be zero. The liquid composition, in an amount of at least 0.05 to 0.3% (by weight), can be used in products which contain water or can be diluted with water such as dispersions of synthetic materials, emulsion paints, adhesives, paper-coating materials, textile softening agents, sizing agents, surfactants, detergents, cleaning and polishing agents, spinning baths, coolants or metal working fluids, leather auxiliaries, and silicone and bitumen emulsions, as agent against material destruction caused by microbes.
    Type: Grant
    Filed: January 28, 1993
    Date of Patent: January 4, 1994
    Assignee: Sterling Winthrop, Inc.
    Inventors: Heinz Eggensperger, Peter Oltmanns, Karl-Heinz Scheler, Karl-Heinz Diehl
  • Patent number: 5276029
    Abstract: Wood preservatives contain a copper salt, a polyamine and a fatty amine and are used for preserving wood from fungi and termites.
    Type: Grant
    Filed: November 1, 1990
    Date of Patent: January 4, 1994
    Assignee: Dr. Wolman GmbH
    Inventors: Reimer Goettsche, Hans-Volker Borck
  • Patent number: 5187194
    Abstract: Wood preservatives which contain a mixture of an N-organyldiazeniumdioxy-metal salt and a complex-forming polymeric nitrogen compound are used for preserving wood.
    Type: Grant
    Filed: October 16, 1990
    Date of Patent: February 16, 1993
    Assignee: Dr. Wolman GmbH
    Inventors: Reimer Goettsche, Wolfgang Reuther
  • Patent number: 5186947
    Abstract: Water-soluble wood preservatives which contain mixtures of a metal compound, a metal-fixing acid and a complexing polymeric nitrogen compound, and methods for protecting wood with such mixtures.
    Type: Grant
    Filed: September 19, 1991
    Date of Patent: February 16, 1993
    Assignee: Dr. Wolman GmbH
    Inventors: Reimer Goettsche, Wolfgang Reuther
  • Patent number: 5135942
    Abstract: A fungicidal composition comprisingA) at least one of 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-batan-2-ol of the formula ##STR1## and 1-(4-phenyl-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl(butan-2-ol of the formula ##STR2## and B) at least one guanidated aliphatic polyamine of the formula ##STR3## in which R.sup.1 represents a branched or unbranched, divalent aliphatic hydrocarbon radical having 3 to 14 carbon atoms,R.sup.2 represents a branched or unbranched, divalent aliphatic hydrocarbon radical having 3 to 14 carbon atoms,X.sup.1, X.sup.2 and X.sup.3 independently of one another represent hydrogen or the radical of the formula ##STR4## and n represents integers from 0 to 16, it being possible for the divalent aliphatic hydrocarbon radicals which represent R.sup.2 to be different from one another if n represents numbers larger than 1, or their acid addition salts.
    Type: Grant
    Filed: January 10, 1991
    Date of Patent: August 4, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stefan Dutzmann, Hans Scheinpflug, Dieter Berg, Wolfgang Kramer
  • Patent number: 5126360
    Abstract: A fungicidal composition comprisingA) 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-ol of the formula ##STR1## and B) at least one guanidated aliphatic polyamine of the formula ##STR2## in which R.sup.1 represents a branched or unbranched, divalent aliphatic hydrocarbon radical having 3 to 14 carbon atoms,R.sup.2 represents a branched or unbranched, divalent aliphatic hydrocarbon radical having 3 to 14 carbon atoms,X.sup.1, X.sup.2 and X.sup.3 independently of one another represent hydrogen or the radical of the formula ##STR3## and n represents integers from 0 to 16, it being possible for the divalent aliphatic hydrocarbon radicals which represents R.sup.2 to be different from one another if n represents numbers larger than 1, or their acid addition salts.
    Type: Grant
    Filed: January 10, 1991
    Date of Patent: June 30, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stefan Dutzmann, Wilhelm Brandes, Dieter Berg, Graham Holmwood
  • Patent number: 5109024
    Abstract: The present invention relates to certain novel polyamine compounds of the formula: ##STR1## wherein Z is a saturated (C.sub.2 -C.sub.6) alkylene moiety, each R group independently is hydrogen, methyl, ethyl, or n-propyl with the provisos that both R groups cannot be hydrogen and that R is hydrogen or methyl when Z is a branched chain alkylene; or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: February 8, 1991
    Date of Patent: April 28, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Nellikunja Prakash, David M. Stemerick, Michael L. Edwards, Terry L. Bowlin
  • Patent number: 4935449
    Abstract: The importance of polyamines in biological systems is discussed as well as the implications of polyamines in the treatment of various diseases. Novel N-substituted-2,3-butadienyl tri- and tetra-aminoalkanes are disclosed as well as their use inthe treatment of diseases and the pharmaceutical compositions.
    Type: Grant
    Filed: August 4, 1988
    Date of Patent: June 19, 1990
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Philippe Bey, David M. Stemerick, Michael L. Edwards, Alan J. Bitonti
  • Patent number: 4559362
    Abstract: This invention relates to an immunopotentiator or an immunopotentiating method using spermidine or its pharmacologically acceptable salt as an active ingredient.
    Type: Grant
    Filed: November 9, 1983
    Date of Patent: December 17, 1985
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Hamao Umezawa, Tomio Takeuchi, Masaaki Ishizuka
  • Patent number: 4507321
    Abstract: Disclosed herein are compositions containing aliphatic di- and polyamine, or agmatine which are useful to regulate, i.e., stimulate or inhibit, epithelial cell growth. The compositions containing low concentrations of these compounds, by virtue of their epithelial cell growth stimulating activity, are useful in promoting wound healing, treating burns, treating ischemic, debubitus and peptic ulcers, plastic and reconstructive surgery, dermatological disorders, promoting autograft and homograft growth, stimulating organ and tissue regeneration in vitro and in vivo, as a component in defined (serum protein-free) media for cultured cells.Compositions containing these compounds in higher concentrations are useful in the inhibition of cell growth and are useful in the treatment of psoriasis and in retardation of fibrosis after injuries to the spinal cord and nervous system. Also disclosed are various methodologies for utilizing such compositions.
    Type: Grant
    Filed: February 17, 1982
    Date of Patent: March 26, 1985
    Assignee: The Research Foundation of State University of New York
    Inventor: Ilene H. Raisfeld