Nitrogen Bonded Directly At 2-position Patents (Class 544/292)
  • Patent number: 6107293
    Abstract: Compounds of formula (I) wherein X is --CH.sub.2 --, --CO-- or direct linkage, Y is --O--, --S-- or --NH--, R.sub.1 is phenyl, R.sub.2 .dbd.H or phenyl and R.sub.3 is H or --CH.sup.3 -- and their pharmaceutically acceptable salts have tachykinin antagonist activity and are useful as pharmaceuticals e.g. for the treatment of pain and migraine.
    Type: Grant
    Filed: July 14, 1999
    Date of Patent: August 22, 2000
    Assignee: Novaris AG
    Inventors: Christopher Simon John Walpole, Mahavir Prashad, Denis Har
  • Patent number: 6040448
    Abstract: Disclosed are compounds of the formula: ##STR1## or pharmaceutically acceptable addition salts thereof, wherein: X, Y and Z are the same or different and represent optionally substituted carbon or nitrogen;R.sub.1 and R.sub.2 independently represent organic or inorganic substituents;R.sub.3 and R.sub.4 are variables independently representing inorganic or organic substituents;A represents C.sub.1 -C.sub.4 alkylene; andR.sub.5, R.sub.6, and R.sub.7 independently represent hydrogen or C.sub.1 -C.sub.6 alkyl,which compounds bind selectively with high affinity to the dopamine D.sub.4 receptor subtype and are therefore of use in treatment of various neuropsychological disorders.
    Type: Grant
    Filed: October 23, 1998
    Date of Patent: March 21, 2000
    Assignee: Neurogen Corporation
    Inventors: William Greenlee, Ashit Gangly, Jan W. F. Wasley
  • Patent number: 5977110
    Abstract: Substituted cyclohexylamines and derivatives thereof are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful as central nervous system agents and are particularly useful as dopaminergic, serotonergic, antipsychotic, and anxiolytic agents.
    Type: Grant
    Filed: March 20, 1998
    Date of Patent: November 2, 1999
    Assignee: Warner-Lambert Company
    Inventors: Thomas R. Belliotti, Suzanne R. Kesten, Thomas A. Pugsley, David J. Wustrow
  • Patent number: 5935973
    Abstract: Compounds of formula I ##STR1## and pharmaceutically acceptable salts thereof in which A is methylene or O; B is methylene or O; g is 0,1,2,3 or 4; R.sub.1 is an optional substituent; U is an alkylene chain optionally substituted by one or more alkyl; Q represents a divalent group containing nitrogen atoms; and T represents CO.HET, have utility in the treatment of central nervous system disorders, for example depression, anxiety, psychoses (for example schizophrenia), tardive dyskinesia, Parkinson's disease, obesity, hypertension, Tourette's syndrome, sexual dysfunction, drug addiction, drug abuse, cognitive disorders, Alzheimer's disease, senile dementia, obsessive-compulsive behavior, panic attacks, social phobias, eating disorders and anorexia, cardiovascular and cerebrovascular disorders, non-insulin dependent diabetes mellitus, hyperglycaemia, constipation, arrhythmia, disorders of the neuroendocrine system, stress, prostatic hypertrophy, and spasticity.
    Type: Grant
    Filed: January 5, 1998
    Date of Patent: August 10, 1999
    Assignee: Knoll Aktiengesellschaft
    Inventors: Alan Martin Birch, David John Heal, Frank Kerrigan, Keith Frank Martin, Patricia Lesley Needham, Bruce Jeremy Sargent
  • Patent number: 5922711
    Abstract: A compound of the formula: ##STR1## wherein --X.sup.3 .dbd.X.sup.2 --X.sup.1 .dbd.N-- is a group of the formula: ##STR2## R.sup.1 is hydrogen or halogen, R.sup.2 is halogen,R.sup.3 is hydrogen, nitro, amino optionally having at least one substituent or a heterocyclic group optionally having at least one substituent,R.sup.4 and R.sup.5 are each hydrogen, or halogen,R.sup.6 and R.sup.8 are each hydrogen, halogen, lower alkyl, hydroxy, lower alkylthio, amino optionally substituted with lower alkyl, or lower alkoxy optionally substituted with a substituent selected from the group consisting of hydroxy, lower alkoxy, amino, lower alkylamino and aryl optionally substituted with lower alkoxy,R.sup.7 is hydrogen or lower alkyl,A is lower alkylene, andQ is O or N--R.sup.9 is hydrogen or acyl,provided that R.sup.3 is not hydrogen when X.sup.1 is C--R.sup.6, in which R.sup.6 is hydrogen, andpharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: September 19, 1997
    Date of Patent: July 13, 1999
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Teruo Oku, Hiroshi Kayakiri, Shigeki Satoh, Yoshito Abe, Yuki Sawada, Takayuki Inoue, Hirokazu Tanaka
  • Patent number: 5869495
    Abstract: A compound of Formula (I) ##STR1## or a tautomeric form thereof and/or a pharmaceutically acceptable salt thereof, and/or a pharmaceutically acceptable solvate thereof, whereinA.sup.1, A.sup.2, A.sup.3, R.sup.2, X, Y and n are as defined herein; a pharmaceutical composition comprising such a compound and the use of such a compound or composition in medicine.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: February 9, 1999
    Assignee: SmithKline Beecham p.l.c.
    Inventors: David Haigh, John Thomas Sime
  • Patent number: 5783576
    Abstract: New compounds of general formula (I) are provided: ##STR1## which are explained in the specification can be prepared by a variety of methods. The compounds may be used in pharmaceutical compositions.
    Type: Grant
    Filed: August 9, 1996
    Date of Patent: July 21, 1998
    Assignee: Boehringer Ingelheim KG
    Inventors: Otto Roos, Georg Speck, Walter Losel, Dietrich Arndts, Wolf-Dietrich Bechtel
  • Patent number: 5753664
    Abstract: A novel compound of the formula:A--Z--Ar.sup.1 1'CO--Ar.sup.2wherein A is a condensed pyrimidinone or condensed pyridazinone ring; Ar.sup.1 and Ar.sup.2 are independently a ring; Z is a divalent group, or a salt thereof which have an excellent antitumor activity.
    Type: Grant
    Filed: March 13, 1996
    Date of Patent: May 19, 1998
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Tetsuya Aono, Shogo Marui, Fumio Itoh, Masuo Yamaoka, Masafumi Nakao
  • Patent number: 5747497
    Abstract: This invention pertains to compounds of Formulae I, II and III, as defined in the disclosure and claims, including all geometric and stereoisomers, N-oxides, agriculturally suitable salts thereof, agricultural compositions containing them and their use as fungicides.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: May 5, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: James Francis Bereznak, Zen-Yu Chang, Thomas Paul Selby, Charlene Gross Sternberg
  • Patent number: 5744472
    Abstract: Disclosed are compounds of the formula ##STR1## or the pharmaceutically acceptable salts thereof wherein the 6-membered A ring may be optionally substituted with up to four groups independently selected from halogen, hydroxy, lower alkyl, or lower alkoxy;Ar represents optionally substituted aryl or heteroarylZ represents carbon or nitrogen provided thatwhere Z is carbon, R.sub.11 represents hydrogen, halogen, hydroxy, lower alkyl, or lower alkoxy, or phenyl optionally substituted with one or two groups selected from hydrogen, halogen, hydroxy, lower alkyl, or lower alkoxy; andwhere Z is nitrogen, R.sub.11 represents an electron pair;R.sub.5 is hydrogen or lower alkyl;L and m represent integers;n is 0, or an integer;R.sub.12 and R.sub.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: April 28, 1998
    Assignee: Neurogen Corporation
    Inventors: Xiao-shu He, Brian de Costa, Jan W. F. Wasley
  • Patent number: 5675006
    Abstract: Novel methods for the synthesis of substituted ureas and guanidines including Terazosin, Prazosin, Doxazosin, Tiodazosin, Trimazosin, Quinasin and Bunazosin (exemplary of 2-amino substituted Quinazolines), Meobentine and Bethanidine and novel intermediates suitable for use in such methods of synthesis are taught.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: October 7, 1997
    Assignee: Brantford Chemicals Inc.
    Inventors: Khashayar Karimian, Keshava Murthy, Darren Hall
  • Patent number: 5674868
    Abstract: Method of treating 5-HT.sub.3 -mediated disorders, which comprises systemic administration of an effective amount of a compound of formula (I) ##STR1## the pharmaceutically acceptable acid addition salt forms and the stereochemically isomeric forms thereof, wherein R.sup.1 and R.sup.2 represent hydrogen, or R.sup.1 and R.sup.2 taken together form a bivalent radical of formula --CH.dbd.CH--CH.dbd.CH-- (a), --CH.dbd.C(Cl)--CH.dbd.CH-- (b) or --CH.dbd.CH--C(Cl).dbd.CH-- (c); n represents 2, 3 or 4; R.sup.3 represents hydrogen or methoxy; m represents 1 or 2; R.sup.4 represents hydrogen, amino or C.sub.1-3 -alkylcarbonylamino; and R.sup.5 represents hydrogen or halo; novel compounds; compositions; processes for preparing novel compounds and intermediates.
    Type: Grant
    Filed: June 16, 1995
    Date of Patent: October 7, 1997
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Georges Henri Paul Van Daele, Jean-Paul Rene Marie Andre Bosmans, Willy Joannes Carolus Van Laerhoven
  • Patent number: 5656632
    Abstract: Disclosed are compounds of the formula ##STR1## or the pharmaceutically acceptable salts thereof wherein the 6-membered A ring may be optionally substituted with up to four groups independently selected from halogen, hydroxy, lower alkyl, or lower alkoxy;Ar represents optionally substituted aryl or heteroarylZ represents carbon or nitrogen provided thatwhere Z is carbon, R.sub.11 represents hydrogen, halogen, hydroxy, lower alkyl, or lower alkoxy, or phenyl optionally substituted with one or two groups selected from hydrogen, halogen, hydroxy, lower alkyl, or lower alkoxy; andwhere Z is nitrogen, R.sub.11 represents an electron pair;R.sub.5 is hydrogen or lower alkyl;L and m represent integers;n is 0, or an integer;R.sub.12 and R.sub.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 12, 1997
    Assignee: Neurogen Corporation
    Inventors: Xiao-shu He, Brian de Costa, Jan W. F. Wasley
  • Patent number: 5646154
    Abstract: Quinazoline compounds represented by general formula (1) or (2) possess an activity of significantly inhibiting the production or secretion of a tumor necrosis factor and are useful as drugs for the treatment of diseases wherein a tumor necrosis factor is considered to be involved in causing those diseases: ##STR1## wherein R.sup.1 through R.sup.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: July 8, 1997
    Assignee: Sumitomo Pharmaceuticals Co., Ltd.
    Inventors: Kenji Irie, Yutaka Ueda, Norio Fujiwara
  • Patent number: 5602168
    Abstract: Disclosed are compounds of the formula ##STR1## or the pharmaceutically acceptable salts thereof wherein the 6-membered A ring may be optionally substituted with up to four groups independently selected from halogen, hydroxy, lower alkyl, or lower alkoxy;Ar represents optionally substituted aryl or heteroarylZ represents carbon or nitrogen provided thatwhere Z is carbon, R.sub.11 represents hydrogen, halogen, hydroxy, lower alkyl, or lower alkoxy, or phenyl optionally substituted with one or two groups selected from hydrogen, halogen, hydroxy, lower alkyl, or lower alkoxy; andwhere Z is nitrogen, R.sub.11 represents an electron pair;R.sub.5 is hydrogen or lower alkyl;L and m represent integers;n is 0, or an integer;R.sub.12 and R.sub.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: February 11, 1997
    Assignee: Neurogen Corporation
    Inventors: Xiao-shu He, Brian de Costa, Jan W. F. Wasley
  • Patent number: 5576322
    Abstract: The invention is directed to certain 2,4-diaminoquinazoline compounds, their pharmaceutically acceptable salts, the pharmaceutical compositions comprising those compounds and their therapeutic methods of use. The compounds possess anti-ischemic activity.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: November 19, 1996
    Assignee: Eisai Co., Ltd.
    Inventors: Yasutaka Takase, Nobuhisa Watanabe, Makoto Matsui, Hironori Ikuta, Teiji Kimura, Takao Saeki, Hideyuki Adachi, Tadakazu Tokumura, Hisatoshi Mochida, Yasunori Akita, Shigeru Souda
  • Patent number: 5543433
    Abstract: Compounds of the formula I ##STR1## where X is hydrogen, halogen, alkyl, alkoxy, trifluoromethyl, cyano or nitro,Y is an amino, methylamino or dimethylamino group,Z is a group CHCH.sub.3, CHOCH.sub.3 or NOCH.sub.3,R is hydrogen or alkyl,A is hydrogen, alkyl, haloalkyl or cycloalkyl,B is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl or the group ##STR2## where W is hydrogen, alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, unsubstituted or substituted aryl or heteroaryl, unsubstituted or substituted aryloxy, arylthio, arylamino or aryl-N-(C.sub.1 -C.sub.6 -alkyl)amino, heteroaryloxy, heteroarylthio, heteroarylamino or heteroaryl-N-(alkyl)amino orA and B, together with the C atom whose substituents they are, are an isocyclic or heterocyclic ring which can also be quinonoid,and fungicides containing these compounds.
    Type: Grant
    Filed: June 3, 1994
    Date of Patent: August 6, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Doetzer, Hubert Sauter, Herbert Bayer, Franz Roehl, Gisela Lorenz, Eberhard Ammermann, Horst Wingert
  • Patent number: 5470975
    Abstract: Novel A-II receptor antagonists have the formula ##STR1## and its isomer ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as defined herein.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: November 28, 1995
    Assignee: E.R. Squibb & Sons, Inc.
    Inventor: Karnail Atwal
  • Patent number: 5411963
    Abstract: Substituted quinazolines of the formula (1): ##STR1## wherein: R.sup.1 to R.sup.4 are independently H, halo, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, halo (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, NO.sub.2, or NH.sub.2,provided thatat least two of R.sup.1 to R.sup.4 are H;Y is H, Cl, X--W--Ar, or O--Alk;X is O, NR.sup.7, or CR.sup.8 R.sup.9 ;Z is H, Cl, OCH.sub.3, CH.sub.3, or --NR.sup.7 --W--Ar, provided that Z can be --NR.sup.7 --W--Ar only if Y is H, Cl, or NR.sup.7 --W--Ar and Z must be --NR.sup.7 --W--Ar if Y is H or Cl, which are plant fungicides, miticides, and insecticides.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: May 2, 1995
    Assignee: DowElanco
    Inventors: Barry A. Dreikorn, Glen P. Jourdan, Robert G. Suhr
  • Patent number: 5403930
    Abstract: A compound of the formula Het--NR--SO.sub.2 --Ph.sup.2 --A--Ph.sup.1 (COOH)(OH) and tautomic form, salts, solvates, C.sub.1-6 alkyl esters and pharmaceutical compositions of the compound. Ph.sup.1 and Ph.sup.2 are benzene rings with the proviso that carboxy and hydroxy are ortho to one another. Het includes an optionally substituted heterocyclic ring which includes conjugated double bonds and binds to nitrogen in NR. The compound is characterized in that A is a bridge which is stable against reduction because it is not azo, and in that R is hydrogen or lower alkyl.The invention also includes the preparation of the compound and its use as a drug, particularly for treating autoimmune diseases.
    Type: Grant
    Filed: October 7, 1993
    Date of Patent: April 4, 1995
    Assignee: Pharmacia AB
    Inventors: Hubert Agback, Leif Ahrgren, Thomas Berglindh, Martin Haraldsson, Goran Smedeg.ang.rd, Lars-Inge Olsson
  • Patent number: 5391737
    Abstract: This invention relates to a new and improved process for the preparation of 6,7-dichloro-1,5-dihydroimidazo[2,1-b]-quinazolin-2[3H]-one of formula ##STR1## (anagrelide), a valuable blood platelet antiaggregative compound. According to the process of the invention the compound of formula (I) is prepared by subjecting a new 2-cyanoiminoquinazoline derivative of the general formula ##STR2## wherein R stands for cyano or a group of the formula COOR.sup.1, in the latter R.sup.1 representing lower alkyl optionally carrying a phenyl substituent, to thermal cyclization in an acidic medium.The invention also relates to new 2-cyanoiminoquinazo-lines of the general formula (III) used for the production of anagrelide and to the preparation of the said compounds.The invention provides an advantageous process for the preparation of anagrelide which is devoid of the drawbacks of the hitherto known processes and renders possible the production of the compound of the formula (I) on industrial scale, too.
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: February 21, 1995
    Assignee: EGIS Gyogyszergyar
    Inventors: Jozsef Reiter, Peter Trinka, Peter Tompe, Eva Szabo, Peter Slegel, Janos Brlik, Agnes Halbauer nee Nagy, Ilona Sztruhar, Magdolna Kenyeres nee Feher, Frigyes Gorgenyi, Margit Csorgo, Szvetlana Zsarnoczai nee Kurnyecova, Sarolta Benko nee Markus, Gabor Gigler, Dezso Danyi, Pal Fekete, Maria Kiraly nee Ignacz
  • Patent number: 5330989
    Abstract: Biphenyl derivatives of cyclobutene-1,2-dione of formula 1 are angiotensin II antagonists and are useful for the treatment of hypertension and congestive heart failure ##STR1## wherein: Y is O, NR.sup.7, NCOR.sup.7 ; or R.sup.5 and Y taken together represent a linking chain of N.dbd.CR.sup.8 N; or R.sup.5 and Y taken together represent a linking chain of (CR.sup.9 R.sup.10).sub.n CON where n=1,2,3,4, or 5;X is N, CR.sup.7 ;Z is N, CR.sup.7 ;R.sup.1 is H, alkyl, benzyl, alkoxyalkyl, phenyl;R.sup.2 is H, alkyl, benzyl, alkoxyalkyl, phenyl, alkoxy, alkyl-OH, perfluoroalkyl, F, Cl, Br, I, NR.sup.7 R.sup.8 ;R.sup.3 is H, alkyl, benzyl, alkoxyalkyl, phenyl, alkoxy, alkyl-OH, perfluoroalkyl, F, Cl, Br, I, NR.sup.7 R.sup.8 ;R.sup.4 is H, NR.sup.7 R.sup.8, OR.sup.1, CN, F, Cl, I, Br, perfluoroalkyl, alkyl, phenyl, alkoxy, alkyl-OH, alkoxyalkyl, --(CH.sub.2).sub.n CO.sub.2 R.sup.1, --(CH.sub.2).sub.n CONR.sup.7 R.sup.8 where n=1, 2, 3, 4, or 5;R.sup.5, R.sup.
    Type: Grant
    Filed: September 11, 1992
    Date of Patent: July 19, 1994
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, William A. Kinney
  • Patent number: 5302718
    Abstract: A compound of the formula Het--NR--SO.sub.2 --Ph.sup.2 --A--Ph.sup.1 (COOH)(OH) and tautomeric form, salts, solvates, C.sub.1-6 alkyl esters and pharmaceutical compositions of the compound. Ph.sup.1 and Ph.sup.2 are benzene rings with the proviso that carboxy and hydroxy are ortho to one another. Het includes an optionally substituted heterocyclic ring which includes conjugated double bonds and binds to nitrogen in NR. The compound is characterized in that A is a bridge which is stable against reduction because it is not azo, and in that R is hydrogen or lower alkyl.The invention also includes the preparation of the compound and its use as a drug, particularly for treating autoimmune diseases.
    Type: Grant
    Filed: November 9, 1992
    Date of Patent: April 12, 1994
    Assignee: Kabi Pharmacia AB
    Inventors: Hubert Agback, Leif Ahrgren, Thomas Berglindh, Martin Haraldsson, Goran Smedegard, Lars-Inge Olsson
  • Patent number: 5286726
    Abstract: This invention relates to certain conjugates of folates and antifolates with difluoroglutamic acid which are useful in the treatment of patients suffering from certain neoplastic diseases including leukemia, melanomas, carcinomas, sarcomas and mixed neoplasias.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: February 15, 1994
    Assignees: The Regents of the University of Michigan, Health Research, Inc., Merrell Dow Pharmaceuticals Inc.
    Inventors: Philippe Bey, James K. Coward, John J. McGuire
  • Patent number: 5234936
    Abstract: There are disclosed compounds of the general formula I: ##STR1## wherein X is H, NR.sup.12 R.sup.13, OR.sup.14, CN, F, Cl, I, Br, perfluoroalkyl, alkyl, alkoxy, alkyl-OH, alkoxyalkyl, --(CH.sub.2).sub.n CO.sub.2 R.sup.14, --(CH.sub.2).sub.n CONR.sup.12 R.sup.13 ;Y is NR.sup.15, NR.sup.18 CR.sup.16 R.sup.17, CR.sup.16 R.sup.17 NR.sup.15 ;R.sup.1 is 5-tetrazolyl, CO.sub.2 R.sup.14, SO.sub.3 H, NHSO.sub.2 CH.sub.3, NHSO.sub.2 CF.sub.3 ;R.sup.2, R.sup.3 is H, alkyl, alkoxy, alkoxyalkyl, alkyl-OH perfluoroalkyl, aralkyl, CN, NO.sub.2, SO.sub.2 R.sup.19, --(CH.sub.2).sub.n CO.sub.2 R.sup.14, --(CH.sub.2).sub.n CONR.sup.12 R.sup.13, OR.sup.14, F, Cl, Br, I, NR.sup.12 R.sup.13 ;R.sup.4 -R.sup.11 is H, F, alkyl, alkoxy, alkoxyalkyl, --OCOR.sup.14, alkyl-OH, perfluoroalkyl, aralkyl, aryl, CN, NO.sub.2, SO.sub.2 R.sup.19, --(CH.sub.2).sub.n CO.sub.2 R.sup.14, --(CH.sub.2).sub.n CONR.sup.12 R.sup.13, OH, OR.sup.14, --NR.sup.12 R.sup.13, any two geminal groups can be O or CH.sub.2 ;R.sup.12, R.sup.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: August 10, 1993
    Assignee: American Home Products Corporation
    Inventors: John L. Primeau, Lloyd M. Garrick, Timothy D. Ocain, Richard M. Soll, Paul J. Dollings
  • Patent number: 5227493
    Abstract: N-fluoro perfluoroheterocyclic sulfonamides of the following Formula I ##STR1## wherein Het.sub.f represents an aromatic perfluoroheterocyclic radical of valency n and each R independently represents a substituted or unsubstituted C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.14 aryl substituted C.sub.1 -C.sub.10 alkyl, C.sub.6 -C.sub.14 aryl, or C.sub.1 -C.sub.10 alkyl substituted C.sub.6 -C.sub.14 aryl group, are novel electrophilic fluorinating agents. Preferably Het.sub.f is a perfluorinated nitrogen-containing aromatic group, especially pyridyl, pyrimidinyl, pyrazinyl or 1,3,5-triazinyl; n is 1; and R is perfluorinated, especially trifluoromethyl.
    Type: Grant
    Filed: August 31, 1990
    Date of Patent: July 13, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Ronald E. Banks
  • Patent number: 5212177
    Abstract: Novel compounds having the formula ##STR1## and its isomer ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and X are as defined herein. These compounds inhibit the action of angiotensin II and are useful, therefore, for example, an antihypertensive agents.
    Type: Grant
    Filed: December 16, 1991
    Date of Patent: May 18, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Michael A. Poss, Karnail S. Atwal
  • Patent number: 5187168
    Abstract: There are disclosed compounds of the general formula I: ##STR1## wherein A is --CR.sup.7 .dbd.CR.sup.8 --;Z is --CR.sup.7 .dbd.CR.sup.8 --;X is H, NR .sup.9 R.sup.10, OR.sup.11, CN, F, Cl, I, Br, perfluoroalkyl, alkyl,alkoxy, alkyl-OH, alkoxyalkyl, --(CH.sub.2).sub.n CO.sub.2 R.sup.11,--(CH.sub.2).sub.n CONR.sup.9 R.sup.10 ;Y is NR.sup.13,NR.sup.13 CR.sup.12 R.sup.14, CR.sup.12 R.sup.14 NR.sup.13 ;R.sup.1 is 5-tetrazolyl, CO.sub.2 R.sup.11,SO.sub.3 H, NHSO.sub.2 CH.sub.3, NHSO.sub.2 CF.sub.3 ;R.sup.2,R.sup.3,R.sup.4,R.sup.7 R.sup.8 is H, alkyl, alkoxy, alkoxyalkyl, alkyl-OH, perfluoroalkyl, aralkyl, CN, NO.sub.2, SO.sub.2 R.sup.13, --(CH.sub.2).sub.n CO.sub.2 R.sup.11,--(CH.sub.2).sub.n CONR.sup.9 R.sup.10, OR.sup.11,F,Cl,Br,I,NR.sup.9 R.sup.10 ;R.sup.5 is alkyl, alkoxy, alkoxyalkyl, alkyl-OH, perfluoroalkyl, aralkyl, H, --CN, NO.sub.2, SO.sub.2 R.sup.13,--(CH.sub.2).sub.n CO.sub.2 R.sup.11, --(CH.sub.2).sub.n CONR.sup.9 R.sup.10, --OH,OR.sup.11,F,Cl,Br,I,NR.sup.9 R.sup.10 ;R.sup.9,R.sup.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: February 16, 1993
    Assignee: American Home Products Corporation
    Inventors: John L. Primeau, Lloyd M. Garrick
  • Patent number: 5153124
    Abstract: Derivatives of ML-236B carboxylic acid, its salts and esters and corresponding lactone have a hydroxy group at the 3"-position and optionally also at the 6'-position. These derivatives may be prepared by the enzymatic hydroxylation of a corresponding ML-236B compound employing an enzyme produced by a microorganism of the genus Streptomyces or Amycolata, especially Streptomyces sp. SANK 62285, Streptomyces sp. SANK 62385, Streptomyces sp. SANK 62485, Streptomyces sp. SANK 62585, Amycolata autotrophica SANK 62781, Amycolata autotrophica subsp. canberrica SANK 62882 or Amycolata autotrophica subsp. amethystina SANK 62981. These derivatives have the ability to inhibit cholesterol biosynthesis.
    Type: Grant
    Filed: August 11, 1989
    Date of Patent: October 6, 1992
    Assignee: Sankyo Company Limited
    Inventors: Kouhei Furuya, Takao Okazaki, Yoshio Tsujita, Seigo Iwado, Kiyoshi Hamano, Masao Kuroda, Jun Yoshikawa, Toshiaki Iwai, Kunio Nakano
  • Patent number: 5120845
    Abstract: The present invention relates to novel positive inotropic and lusitropic 3,5-dihydroimidazo[2,1-b]quinazolin-2(1H)-one derivatives having positive inotropic and lusitropic properties which are useful in the treatment of warm-blooded animals suffering from Congestive Heart Failure. Pharmaceutical compositions containing said compounds as an active ingredient. Methods of preparing said compounds and pharmaceutical compositions.
    Type: Grant
    Filed: July 24, 1991
    Date of Patent: June 9, 1992
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Eddy J. E. Freyne, Alfons H. M. Raeymaekers
  • Patent number: 5064833
    Abstract: 2,4-diaminoquinazoline compounds are inhibitors of the H.sup.+ K.sup.+ ATPase enzyme and useful for the treatment of diseases of the stomach based on excessive gastric acid secretion. A compound of the invention is 2-[2-methyl-4-fluorophenyl)amino]-4-(N-methylphenylamino)quinazoline.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: November 12, 1991
    Assignee: Smithkline Beecham Intercredit B.V.
    Inventors: Robert J. Ife, Thomas H. Brown, Colin A. Leach, David J. Keeling
  • Patent number: 5053411
    Abstract: This invention pertains to novel substituted N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides useful as analgesics, and methods of administering analgesia, which comprises the systemic administration to mammals of such compounds, and pharmaceutical compositions containing such compounds, wherein the novel compounds have the general formula: ##STR1## including optically active isomeric forms, and the pharmaceutically acceptable acid addition salts thereof, wherein R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are defined in the disclosure.
    Type: Grant
    Filed: April 20, 1989
    Date of Patent: October 1, 1991
    Assignee: Anaquest, Inc.
    Inventors: Jerome R. Bagley, Nhora L. Lalinde, Bao-Shan Huang, H. Kenneth Spencer
  • Patent number: 4959368
    Abstract: A pharmaceutical composition comprising a pyrimidine represented by the following formula ##STR1## wherein R.sup.1 represents a hydrogen atom, an acyl group having 2 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, an alkoxycarbonylmethyl group having 3 to 5 carbon atoms, a 3,4-dimethoxybenzoyl group or a 3,4-methylenedioxybenzyl group,R.sup.2 represents a hydrogen atom, an amino group, a monoalkylamino group having 1 to 4 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an alkoxycarbonyl group having 2 to 4 carbon atoms,R.sup.3 represents a hydrogen atom, an alkoxycarbonyl group having 2 to 4 carbon atoms, a dialkylaminocarbonyl group having 1 to 9 carbon atoms in each alkyl moiety, an alkoxy group having 1 to 5 carbon atoms, or a hydroxyethyl group, R.sup.2 and R.sup.3, together with the carbon atoms to which they are bonded, may form a 5- to 7-membered carbocyclic ring or a heterocyclic ring having N, O or S as the hetero atom, and R.sup.
    Type: Grant
    Filed: October 22, 1987
    Date of Patent: September 25, 1990
    Assignees: Mitsui Petrochemical Industries Ltd., Mitsui Pharmaceuticals, Inc.
    Inventors: Akira Awaya, Takuo Nakano, Hisashi Kobayashi, Ken E. Tan, Kazutoshi Horikomi, Tadayuki Sasaki, Keiichi Yokoyama, Hiroyasu Ohno, Kozi Kato, Takumi Kitahara, Ikuo Tomino, Shigeru Isayama
  • Patent number: 4788199
    Abstract: Amides of formula: ##STR1## in which A is ##STR2## V and W are H, halogen, alkyl (1-3C), alkoxy (1-3C), NO.sub.2 or CF.sub.3, Z is bound in the ortho or para position with respect to B and is phenyl, optionally substituted, thienyl or pyridyl, the chain X--(CH.sub.2).sub.n --(CHR).sub.m --CO--NR.sub.1 R.sub.2 is bound in the ortho or para position with respect to B,R is H or alkyl (1-3C),R.sub.1 and R.sub.2 are alkyl (1-6C), cycloalkyl (3-6C), phenyl, phenylalkyl, cycloalkylalkyl, alkenyl (3-6C),R.sub.1 and R.sub.2 can also form, with the nitrogen atom to which they are attached, a pyrrolidine, piperidine, morpholine or thiomorpholine ring,X is >CH--R.sub.3, >N--R.sub.4, >SO, >SO.sub.2, >O or >S,R.sub.3 is H, alkyl (1-3C),R.sub.4 is alkyl (1-3C)m=0 or 1 and n=0, 1 or 2,provided that, if X is >SO, >SO.sub.2 or >N--R.sub.4 , the sum m+n is equal to at least 1, that, when A and B are N and Z is in the para position with respect to B, X cannot denote the group >CH--R.sub.
    Type: Grant
    Filed: March 11, 1988
    Date of Patent: November 29, 1988
    Assignee: Rhone-Poulenc Sante
    Inventors: Jesus Benavides, Marie-Christine Dubroeucq, Gerard Le Fur, Christian Renault
  • Patent number: 4788204
    Abstract: Amides of formula: ##STR1## in which A is ##STR2## V and W are H, halogen, alkyl (1-3C), alkoxy (1-3C), NO.sub.2 or CF.sub.3, Z is bound in the ortho or para position with respect toB and is phenyl, optionally substituted, thienyl or pyridyl, the chain X-(CH.sub.2).sub.n --(CHR).sub.m --CO--NR.sub.1 R.sub.2 is bound in the ortho or para position with respect to B,R is H or alkyl (1-3C),R.sub.1 and R.sub.2 are alkyl (1-6C), cycloalkyl (3-6C), phenyl, phenylalkyl, cycloalkylalkyl, alkenyl (3-6C),R.sub.1 and R.sub.2 can also form, with the nitrogen atom to which they are attached, a pyrrolidine, piperidine, morpholine or thiomorpholine ring,X is >CH--R.sub.3, >N--R.sub.4, >SO, >SO.sub.2, >O or >S,R.sub.3 is H, alkyl (1-3C),R.sub.4 is alkyl (1-3C)m=0 or 1 and n=0, 1 or 2,provided that, if X is >SO, >SO.sub.2 or >N--R.sub.4, the sum m+n is equal to at least 1, that, when A and B are N and Z is in the para position with respect to B, X cannot denote the group >CH--R.sub.
    Type: Grant
    Filed: May 28, 1986
    Date of Patent: November 29, 1988
    Assignee: Rhone-Poulenc Sante
    Inventors: Jesus Benavides, Marie-Christine Dubroeucq, Gerard LeFur, Christian Renault
  • Patent number: 4761416
    Abstract: Pharmaceutical compositions comprising, or compositions consisting essentially of, compounds according to the formula ##STR1## or an optical isomer thereof are disclosed, wherein the substituents A, Z and R.sup.1 are defined herein. The invention is also directed to certain compounds of the above class. The compounds of Formula I are cyclic AMP phosphodiesterase inhibitors useful as antithrombotic and inotropic agents and the like in mammals.
    Type: Grant
    Filed: July 25, 1986
    Date of Patent: August 2, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: John H. Fried, Michael C. Venuti
  • Patent number: 4739056
    Abstract: Compounds are disclosed according to the formula ##STR1## or an optical isomer thereof. The compounds of Formula I are cyclic AMP phosphodiesterase inhibitors useful as antithrombotic and inotropic agents and the like in mammals.
    Type: Grant
    Filed: November 26, 1986
    Date of Patent: April 19, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Michael C. Venuti
  • Patent number: 4675047
    Abstract: The invention concerns novel compounds of the formula I ##STR1## The compounds are herbicides and in further embodiments the invention provides: processes for the preparation of compounds of formula I; intermediates useful in the preparation of compounds of formula I; compositions containing as active ingredient compounds of formula I; and processes for severely damaging or killing unwanted plants by applying to the plants or to the growth medium of the plants an effective amount of a compound of formula I.
    Type: Grant
    Filed: June 16, 1981
    Date of Patent: June 23, 1987
    Inventors: Alexander Serban, Wendy A. Jensen
  • Patent number: 4672116
    Abstract: Quinazoline derivatives having an oxy substituent in 5 and 6 positions are described. The novel quinazoline derivatives are useful as cardiotonic agents.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: June 9, 1987
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Victor T. Bandurco, Stanley C. Bell, John H. Dodd, Robert Falotico, Charles F. Schwender, Alfonso J. Tobia
  • Patent number: 4622398
    Abstract: 2-Permissibly-substituted-6-dialkylaminotetrahydroquinazolines, receptor agonists.
    Type: Grant
    Filed: June 24, 1985
    Date of Patent: November 11, 1986
    Assignee: Eli Lilly and Company
    Inventor: Bennett C. Laguzza
  • Patent number: 4608383
    Abstract: The present invention provides aryloxypropanolamines of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, are hydrogen or halogen atoms or lower alkyl, cyano, carboxamide, hydroxyl, lower acyloxy, lower alkoxy, lower alkenyloxy or aryl lower alkoxy radicals, R.sub.5 and R.sub.6, which may be the same or different, are hydrogen atoms or lower alkyl radicals, X is a straight or branched alkylene chain containing 2 to 6 carbon atoms, A is a mono-, bi- or tricyclic heteroaromatic or hydroheteroaromatic radical or, when at least one of the symbols R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is other than a hydrogen atom, may also be a phenyl radical, with the proviso that when A is a uracil-6-yl radical, the 5-position of the uracil moiety does not contain a hydrogen atom, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.
    Type: Grant
    Filed: October 3, 1983
    Date of Patent: August 26, 1986
    Assignee: Boehringer Mannheim GmbH
    Inventors: Fritz Wiedemann, deceased, Wolfgang Kampe, Karl Dietmann, deceased, Gisbert Sponer
  • Patent number: 4588725
    Abstract: 2-Piperazinyl-quinazolines or pharmaceutically acceptable acid addition salts thereof are useful as neuroleptic and anti-hypertensive agents.
    Type: Grant
    Filed: November 10, 1983
    Date of Patent: May 13, 1986
    Assignee: Sandoz Ltd.
    Inventor: Peter Neumann
  • Patent number: 4582525
    Abstract: This invention relates to N-(heterocyclicaminocarbonyl)-o-alkenylbenzenesulfonamides which are useful as agricultural chemicals.
    Type: Grant
    Filed: August 3, 1984
    Date of Patent: April 15, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Chi-wan Chen, Gregory W. Schwing
  • Patent number: 4578459
    Abstract: Heterocyclic compounds which are inhibitors of histamine activity, in particular, inhibitors of H-2 histamine receptors. A specific compound of this invention is 2-[2-(4-methyl-5-imidazolylmethylthio)ethylamino]-4-pyrimidone.
    Type: Grant
    Filed: June 8, 1984
    Date of Patent: March 25, 1986
    Assignee: SmithKline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Ganellin
  • Patent number: 4540696
    Abstract: The present invention relates to new derivatives of formula: ##STR1## in which: R.sub.3 denotes a halogen, preferably chlorine, or a nitro group,R.sub.4 represents hydrogen or a lower alkyl group having from 1 to 4 atoms of carbon,R.sub.5 represents an atom of halogen, preferably chlorine or fluorine.It also relates to a process for preparing products of formula (II) and to the drugs containing at least one product of formula (II).
    Type: Grant
    Filed: February 3, 1983
    Date of Patent: September 10, 1985
    Assignee: Sanofi S.A.
    Inventors: Kathleen Biziere, Andre Hallot, Jean-Paul Kan
  • Patent number: 4528026
    Abstract: Pyrimidine compounds of the formula: ##STR1## in which R.sub.1 is alkyl, one of X.sub.1, X.sub.2, X.sub.3 is chlorine or bromine and the two others are respectively --NR.sub.1 R.sub.2 and --NR.sub.3 R.sub.4 in which R.sub.2 and R.sub.3 are, independently of one another, hydrogen, alkyl, cycloalkyl, aryl or aryl substituted by alkyl, hydroxy, chlorine, bromine or ##STR2## wherein R is hydrogen or alkyl, or form together with the nitrogen atom to which they are linked a nitrogenous heterocyclic radical other than piperazino and substituted piperazino, R.sub.4 and R.sub.5 are, independently of one another, hydrogen, alkyl, cycloalkyl, aryl or aryl substituted by alkyl, hydroxy, chlorine, bromine or ##STR3## wherein R is as defined above, or form together with the nitrogen atom to which they are linked a nitrogenous heterocyclic radical other than piperazino and substituted piperazino, at least one of the substituents --NR.sub.1 R.sub.2, --NR.sub.3 R.sub.4 being NH.sub.
    Type: Grant
    Filed: September 30, 1980
    Date of Patent: July 9, 1985
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Daniel Balde, Gerard E. M. Boutemy
  • Patent number: 4499092
    Abstract: The present invention relates to novel derivatives of 4-phenyl quinazoline of general formula: ##STR1## in which R.sub.2 is H or halogen or R.sub.1 is a hydroxyamino derivative of type ##STR2## in which at least R.sub.3 or R.sub.4 comprises an OH group or ##STR3## in which R.sub.5 comprises an OH group or ##STR4## it also relates to the drugs which may be used as minor tranquilizers, hypnotics and antiepileptics containing a product of formula (I).
    Type: Grant
    Filed: October 19, 1982
    Date of Patent: February 12, 1985
    Assignee: Sanofi
    Inventors: Andre Hallot, Kathleen Biziere
  • Patent number: 4492596
    Abstract: This invention relates to 1-benzopyransulfonamides, 1-benzothiopyransulfonamides, 1-benzoxepinsulfonamides and 1-benzothiepinsulfonamides which are useful as plant growth regulants and in particular as herbicides.
    Type: Grant
    Filed: August 11, 1982
    Date of Patent: January 8, 1985
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Robert J. Pasteris
  • Patent number: 4435205
    Abstract: N-(Heterocycliccarbamoyl)arylsulfonamides, such as N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide , methanesulfonate are useful for plant growth retardation, brush control and weed control in crops.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: March 6, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: James J. Reap
  • Patent number: RE34201
    Abstract: This invention pertains to novel substituted N/aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides useful as analgesics, and methods of administering analgesia, which comprises the systemic administration to mammals of such compounds, and pharmaceutical compositions containing such compounds, wherein the novel compounds have the general formula: ##STR1## including optically active isomeric forms, and the pharmaceutically acceptable acid addition salts thereof, wherein R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are defined in the disclosure.
    Type: Grant
    Filed: April 14, 1992
    Date of Patent: March 23, 1993
    Assignee: Anaquest, Inc.
    Inventors: Jerome R. Bagley, Nhora L. Lalinde, Bao-Shan Huang, H. Kenneth Spencer