Nitrogen Attached Indirectly To The Hetero Ring By Acyclic Nonionic Bonding Patents (Class 549/366)
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Patent number: 6248907Abstract: The invention relates to R-2-[3-([1,4]benzodioxan-2-ylmethylamino)-1-propyl]-3(2H)-pyridazinone of formula (1), and to S-2-[3-([1,4]benzodioxan-2-ylmethylamino)-1-propyl]-3(2H)-pyridazinone of formula (2), and to acid-addition salts thereof as well as pharmaceutical compositions containing these compounds. Furthermore, the invention relates to a process for the preparation of the above compounds. The new starting compounds of formulae (4) and (5) are also involved in the scope of the invention. The compounds according to the invention possess &agr;1- and &agr;2-adrenoceptor antagonistic effects and urogenital selectivity. Thus, they are useful for the treatment of the benign prostate hyperplasia.Type: GrantFiled: August 28, 2000Date of Patent: June 19, 2001Assignee: Gyogyszerkutato Intezet Kft.Inventors: Péter Mátyus, László Hársing, Marianne Tapfer née Karim, Judit Kosáry, Ágnes Papp née Behr, Antal Simay, Yemane Tilahun, Éva Tomori née Joszt, Edit Horváth, Katalin Horváth, Ildikó Varga, Erzsébet Zára née Kaczián, Margit Bidló née Iglóy, Alice Druga, György Rabloczky, Márta Varga, Egon Kárpáti, Endre Kasztreiner, István Király, Ildikó Máthé née Gyóry, György Máthé, László Sebestyén, Nándor Makk
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Patent number: 6232475Abstract: The present invention relates to a process for preparing fluorine-containing phenethylamines which is characterized in that, in a first step, a substituted bromobenzene is reacted with an N-vinylimide in the presence of a palladium catalyst, in a second step, the resulting substituted &bgr;-iminovinylbenzene is hydrogenated catalytically and in a third step, the substituted &bgr;-iminovinylbenzene obtained in the second step is cleaved. This process also provides access to novel &bgr;-iminovinyl- and &bgr;-iminoethylbenzenes.Type: GrantFiled: December 16, 1999Date of Patent: May 15, 2001Assignee: Bayer AktiengesellschaftInventors: Peter Müller, Albrecht Marhold
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Patent number: 6222050Abstract: Disclosed are optically active alcohols having formula (1) and (2) wherein R is (R)-1-phenylethylamino or (S)-1-phenylethylamino. The active alcohols can be prepared by acylating a racemate of formula (3) in the presence of a hydrolase, followed by alcoholysis or hydrolysis. R in formula (3) is the same as that defined for formula (1) and (2).Type: GrantFiled: March 23, 2000Date of Patent: April 24, 2001Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Koji Kawamura, Masahiro Ueno, Masashi Suzuki, Makoto Yanai, Toshihiro Takahashi, Koichi Itoh
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Patent number: 6194411Abstract: The invention relates to R-2-[3-([1,4]benzodioxan-2-ylmethylamino)-1-propyl]-3(2H)-pyridazionone of formula (1) and to S-2-[3-([1,4]benzodioxan-2-ylmethylamino)-1-propyl]-3(2H)-pyridazionone of formula (2) and to acid-addition salts thereof as well as pharmaceutical compositions containing these compounds. Furthermore, the invention relates to a process for the preparation of the above compounds. The new starting compounds of formula (4) and (5) are also involved in the scope of the invention. The compounds according to the invention possess &agr;1- and &agr;2-adrenoceptor antagonistic effects and urogenital selectivity. Thus, they are useful for the treatment of the benign prostate hyperplasia.Type: GrantFiled: July 20, 1998Date of Patent: February 27, 2001Assignee: Gyogyszerkutato Intezet Kft.Inventors: Péter Mátyus, László Hársing, Mariann née Tapfer Karim, Judit Kosáry, Ágnes née Behr Papp, Antal Simay, Yemane Tilahun, Éva née Joszt Tomori, Edit Horváth, Katalin Horváth, Ildikó Varga, Erzsébet née Kaczián Zára, Margit née Iglóy Bidló, Alice Druga, György Rabloczky, Márta Varga, Egon Kárpáti, Endre Kasztreiner, István Király, Ildikó née Gyóry Máthé, György Máthé, László Sebestyén, Nándor Makk
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Patent number: 6162810Abstract: A new family of inadone and tetralone tubulin-binding compounds (TBs) is disclosed. Unlike classical TBs, which inhibit mitosis among affected dividing cells, the TBs of the invention possess two unique properties: (1) they induce apoptosis among stationary phase (non-dividing) malignant cells, yet do not impair the viability of normal nonproliferating cells; and, (2) they affect cells which have acquired MDR more powerfully than they affect cells without MDR. Thus, the TBs of the invention provide means to target malignant cells for chemotherapy, even after previous therapies have failed, without affecting normal cells and tissues in the host.Type: GrantFiled: September 4, 1998Date of Patent: December 19, 2000Assignee: The Regents of the University of CaliforniaInventors: Dennis A. Carson, Hsien C. Shih, Howard B. Cottam, Lorenzo Leoni
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Patent number: 6160005Abstract: A preventive and/or therapeutic medicament for circadian rhythm sleep disorders such as jet lag syndrome which comprises as an active ingredient an alkylenedioxybenzene derivative represented by the following formula (I) wherein m represent an integer of from 2 to 5, and n represents an integer of from 1 to 3, such as 5-[3-[(2S)-(1,4-benzodioxan-2-yl-methyl)amino]propoxy]-1,3-benzodioxol, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: May 19, 1998Date of Patent: December 12, 2000Assignee: Mitsubishi Chemical CorporationInventors: Shigenobu Shibata, Takahiro Moriya, Michikazu Abe
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Patent number: 6143788Abstract: Selected bis-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.Type: GrantFiled: January 21, 1998Date of Patent: November 7, 2000Assignee: G.D. Searle & Co.Inventors: Daniel P. Getman, Gary A. Decrescenzo, John N. Freskos, Michael L. Vazquez, James A. Sikorski, Belekudru Devadas, Srinivasan RAJ Nagarajan, David L. Brown, Joseph J. McDonald
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Patent number: 6143747Abstract: Bis-sulfonamido hydroxyethylamino compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to retroviral protease inhibiting compounds of the formula: ##STR1## or a pharmaceutically acceptable salt, prodrug or ester thereof, wherein the variables are as defined herein.Type: GrantFiled: February 26, 1998Date of Patent: November 7, 2000Assignee: G. D. Searle & Co.Inventors: John N. Freskos, Daniel P. Getman, John J. Talley, James A. Sikorski
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Patent number: 6130251Abstract: The invention relates to new alkoximinoacetic acid amides, a process for their preparation and their use as agents for combating pests.Type: GrantFiled: July 23, 1997Date of Patent: October 10, 2000Assignee: Bayer AktiengesellschaftInventors: Thomas Seitz, Gerd Hanssler, Klaus Stenzel
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Patent number: 6080767Abstract: The compounds according to the invention are substituted N-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides of formula I herein which exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More especially, they are Factor Xa inhibitors. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, methods for their preparation and their use, which are for treating a patient suffering from, or subject to, conditions which can be ameliorated by the administration of an inhibitor of Factor Xa.Type: GrantFiled: June 27, 1997Date of Patent: June 27, 2000Assignee: Aventis Pharmaceuticals Products Inc.Inventors: Scott I. Klein, Kevin R. Guertin, Alfred P. Spada
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Patent number: 6080338Abstract: Described are novel water soluble photochromic naphthopyran and benzopyran compounds having an alkylaminoalkylamino group on the pyran portion or on the pyran portion and the naphtho- or benzo-portion thereof. These compounds may be represented by one of the following graphic formula: ##STR1## wherein B and/or B' is an alkylaminoalkylamino-substituted aryl group and R.sub.1 may also be an alkylaminoalkylamino group. Articles such as ophthalmic lenses or other plastic transparencies and coating compositions such as paints and inks that incorporate the novel water soluble compounds are also described.Type: GrantFiled: March 5, 1999Date of Patent: June 27, 2000Assignee: Transitions Optical, Inc.Inventor: Anil Kumar
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Patent number: 6020503Abstract: An industrial method for preparation of a 1,4-benzodioxane derivative (1), which comprises reacting a diol compound (2) with a carbonating agent to prepare a carbonate compound (3) and after removal of the protective group, cyclizing it by heating or by treating with a base or a fluoride salt.Type: GrantFiled: January 11, 1999Date of Patent: February 1, 2000Assignee: Daiso Co., Ltd.Inventors: Yoshiro Furukawa, Kazuhiro Kitaori, Shouhei Matsui
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Patent number: 5965607Abstract: This invention relates to novel substituted 1,4-benzodioxine compounds having antidiabetic, antihyperglycemic, and antiobesity properties represented by the formula ##STR1## wherein R.sup.1 and R.sup.6 are independently hydrogen, C.sub.1 to C.sub.6 alkyl, trifluoromethyl, cyano, C.sub.1 to C.sub.6 alkoxy, or halogen;R.sup.2 is hydrogen or C.sub.1 to C.sub.6 trialkylsilyl; R.sup.3 is hydrogen or C.sub.1 to C.sub.6 alkoxycarbonyl;or R.sub.2 and R.sup.3 are joined to form the oxazolidinone ring ##STR2## R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1 to C.sub.6 alkyl;R.sup.7 and R.sup.8 are independently OR.sup.9 or NR.sup.10 R.sup.11 ;R.sup.9 is hydrogen, C.sub.1 to C.sub.12 alkyl, C.sub.1 to C.sub.12 cycloalkyl, C.sub.1 to C.sub.12 silylalkyl, phenyl, naphthyl phenyl C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkoxy C.sub.1 to C.sub.6 alkyl, pyridyl, thiophenyl, furanyl, imidazolyl, oxazolyl, --CHR.sup.12 COOR.sup.13 --CHR.sup.12 C(O)R.sup.13, --CHR.sup.12 CONR.sup.10 R.sup.11, --CHR.sup.12 OCOOR.Type: GrantFiled: December 18, 1997Date of Patent: October 12, 1999Assignee: American Home Products CorporationInventor: Aranapakam M. Venkatesan
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Patent number: 5948909Abstract: The invention relates to a method for the stereoselective preparation of a hetero-bicyclic alcohol enantiomer, characterized in that a substantially pure enantiomer of the general formula ##STR1## is prepared from a compound of the general formula ##STR2## wherein the variable are as defined as in claim 1. The method comprises the following successive reaction steps:(i) reaction with a substantially enantiomerically pure compound of the general formula ##STR3## wherein Z, R.sub.3 and R.sub.4 are defined as in claim 1; (ii) subjection of the compound formed to a deprotection/ring-closure reaction;(iii) optionally deprotection of the hydroxy group of the ring-closed product.The invention further relates to enantiomerically pure intermediates, the preparation of these intermediates and the preparation of a starting compound.Type: GrantFiled: January 22, 1997Date of Patent: September 7, 1999Assignee: Duphar International Research B.V.Inventors: Nicolaas Buizer, Chris G. Kruse, Klara M. Schenk, Belal Shadid
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Patent number: 5936102Abstract: The present invention is drawn to a process for preparing a 2,2,3,3-tetrafluoro-1,4-benzodioxane, by cyclocondensing a o-(2-bromo-tetrafluoroethoxy)-phenol in the presence of an acid binder.Type: GrantFiled: July 23, 1998Date of Patent: August 10, 1999Assignee: Bayer AktiengesellschaftInventors: Vera Yakovlevna Popkova, Albrecht Marhold
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Patent number: 5925675Abstract: N-sulfonyliminodithio compounds have the formula (I), in which R.sup.1 and R.sup.2 stand for optionally substituted alkyl, alkenyl or alkinyl, and Ar stands for optionally substituted aryl; also disclosed are processes for preparing these compounds and their use for plant and material protection.Type: GrantFiled: February 18, 1998Date of Patent: July 20, 1999Assignee: Bayer AktiengesellschaftInventors: Hermann Uhr, Martin Kugler, Heinrich Schrage
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Patent number: 5919814Abstract: The invention relates to compound of general formula (I): ##STR1## wherein: Z represents O or CH.sub.2n is from 0 to 4R, X and Y are as defined in the description, andA represents ##STR2## wherein R.sup.1, R.sup.2, R.sup.6, R.sup.7 and T' are as defined in the description,and medicinal products containing the same are useful in treating or in preventing melatoninergic disorders.Type: GrantFiled: April 24, 1998Date of Patent: July 6, 1999Assignee: Adir et CompagnieInventors: Gerald Guillaumet, Isabelle Charton, Ahmed Mamai, Pierre Renard, Bruno Pfeiffer, Philippe Delagrange, Beatrice Guardiola
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Patent number: 5879592Abstract: Described are novel water soluble photochromic naphthopyran and benzopyran compounds having an alkylaminoalkylamino group on the naphtho- or benzo-portions and/or pyran portions thereof. These compounds may be represented by one of the following graphic formulae: ##STR1## wherein R.sub.1 is an alkylaminoalkylamino group. Articles such as ophthalmic lenses or other plastic transparencies and coating compositions such as paints and inks that incorporate the novel water soluble compounds are also described.Type: GrantFiled: December 10, 1997Date of Patent: March 9, 1999Assignee: PPG Industries, Inc.Inventor: Anil Kumar
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Patent number: 5801179Abstract: The present invention is concerned with compounds having the formula ##STR1## the pharmaceutically acceptable acid addition salts thereof, and the stereochemically isomeric forms thereof, wherein R.sup.1 is hydrogen or C.sub.1--6 alkyl; R.sup.2 is hydrogen or C.sub.1- 6 alkyl; R.sup.3 is C.sub.1-6 alkyl, hydroxy, cyano, halo, C.sub.1-6 alkyloxy, aryloxy, arylmethoxy, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkyl--S--, C.sub.1-6 alkyl(S.dbd.O)--, C.sub.1-6 alkylcarbonyl; R.sup.4 is hydrogen, halo, hydroxy, C.sub.1-6 alkyl, or C.sub.1-6 alkyloxy; or R.sup.3 and R.sup.4 taken together form a bivalent radical; R.sup.5 and R.sup.6 each independently are hydrogen, halo, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, aryloxy or arylmethoxy; R.sup.7 is hydrogen; Alk.sup.1 is C.sub.2-5 alkanediyl; Alk.sup.2 is C.sub.2-15 alkanediyl; Q is a heterocyclic ring containing at least one nitrogen atom or a radical of formula ##STR2## Pharmaceutical compositions, preparations and use as a medicine are described.Type: GrantFiled: June 2, 1997Date of Patent: September 1, 1998Assignee: Janssen Pharmaceutica, NVInventors: Guy Rosalia Eugene Van Lommen, Marcel Frans Leopold De Bruyn, Piet Tom Bert Paul Wigerinck
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Patent number: 5780650Abstract: A novel process for preparing a 1,4 benzodioxane derivative shown by the formula (1) which is a useful intermediate of circulatory drugs and drugs for psychoneurosis, characterized in sulfonating a phenoxypropanediol with a sulfonyl halide, eliminating the protective group, and then cyclizing the sulfonated compound by treating with a base followed by, if necessary, further sulfonation. ##STR1## In the above formula, R.sup.1 is H, RSO.sub.2, R is alkyl, phenyl which may be substituted with alkyl, R.sup.2, R.sup.3, R.sup.4 are H, halogen, OH, nitro, cyano, formyl, COOH, alkoxycarbonyloxy, alkyl, alkoxy, haloalkyl, N,N-dialkylamino, alkylcarbonyl, alkoxycarbonyl, phenyl which may be substituted by alkyl, etc.Type: GrantFiled: September 24, 1997Date of Patent: July 14, 1998Assignee: Daiso Co., Ltd.Inventors: Yoshiro Furukawa, Kazuhiro Kitaori, Keishi Takenaka
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Patent number: 5708020Abstract: A compound which is selected from those of formula (I) : ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description,its optical isomers,and its addition salts thereof with a pharmaceutically-acceptable acid or base,and medicinal products containing the same which are useful for treating a disorder of the melatoninergic system.Type: GrantFiled: March 11, 1996Date of Patent: January 13, 1998Assignee: Adir Et CompagnieInventors: Michel Langlois, Pierre Renard, Gerard Adam
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Patent number: 5703115Abstract: The present invention is concerned with vasoconstricive ?benzodioxan, benzofuran or benzopyran)alkylamino!alkyl substituted guanidines having the formula ##STR1## the pharmaceutically acceptable acid addition salts thereof, and the stereochemically isomeric forms thereof, wherein X is O, CH.sub.2 or a direct bond; R.sup.1 is hydrogen or C.sub.1-6 alkyl; R.sup.2 is hydrogen, C.sub.1-6 alkyl, C.sub.3-6 alkenyl or C.sub.3-6 alkynyl; R.sup.3 is hydrogen or C.sub.1-6 alkyl; or R.sup.2 and R.sup.3 may be taken together to form a bivalent radical of formula --(CH.sub.2).sub.m --, wherein m is 4 or 5; or R.sup.1 and R.sup.2 taken together may form a bivalent radical of formula --CH.dbd.CH-- or of formula --(CH.sub.2).sub.n --, wherein n is 2, 3 or 4; or R.sup.3 may represent a bond when R.sup.1 and R.sup.2 taken together form a bivalent radical of formula --CH.dbd.CH--CH.dbd., --CH.dbd.CH--N.dbd., or --CH.dbd.N--CH.dbd.; R.sup.4 is hydrogen or C.sub.1-6 alkyl; Alk.sup.1 is a bivalent C.sub.Type: GrantFiled: April 15, 1996Date of Patent: December 30, 1997Assignee: Janssen Pharmaceutica, N.V.Inventors: Guy Rosalia Eugene Van Lommen, Marcel Frans Leopold De Bruyn, Walter Jacobus Joseph Janssens
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Patent number: 5656627Abstract: The present invention relates to novel classes of compounds which are inhibitors of interleukin-1.beta. converting enzyme. The ICE inhibitors of this invention are characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting ICE activity and consequently, may be advantageously used as agents against interleukin-1 mediated diseases, including inflammatory diseases, autoimmune diseases and neurodegenerative diseases. This invention also relates to methods for inhibiting ICE activity and methods for treating interleukin-1 mediated diseases using the compounds and compositions of this invention.Type: GrantFiled: March 17, 1995Date of Patent: August 12, 1997Assignee: Vertex Pharmaceuticals, Inc.Inventors: Guy W. Bemis, Julian M. C. Golec, David J. Lauffer, Michael D. Mullican, Mark A. Murcko, David J. Livingston
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Patent number: 5646147Abstract: Acaricidal, insecticidal and nematicidal substituted (hetero)arylalkyl ketone oxime O-ethers, processes for their preparation, agents containing them, and their use as pesticides.The invention relates to compounds of the formula ##STR1## in which Ar.sup.1 and Ar.sup.2 are aryl or heteroaryl, each of which is optionally substituted, and R is an optionally substituted aliphatic or alicyclic radical, to processes for their preparation, and to agents containing these compounds, and to their use for controlling animal pests.Type: GrantFiled: April 20, 1994Date of Patent: July 8, 1997Assignee: Hoechst AktiengesellschaftInventors: Birgit Kuhn, Gerhard Salbeck, deceased, Uwe Doller, Stefan Schnatterer, Hans-Herbert Schubert, Werner Knauf, Anna Waltersdorfer, Manfred Kern
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Patent number: 5604256Abstract: Compounds of formula (I): ##STR1## (in which: R is hydrogen, methyl or hydroxy; X is alkyl, alkenyl, cycloalkyl, aryl, aralkyl, or a heterocyclic group; A is a single bond, or an alkylene, alkenylene, alkynylene or alkadienylene group; Y is hydrogen, aryl, cycloalkyl or a heterocyclic group) have the ability to inhibit the biosynthesis of cholesterol, and can thus be used for the treatment and prophylaxis of diseases relating to high blood cholesterol levels.Type: GrantFiled: December 14, 1994Date of Patent: February 18, 1997Assignee: Sankyo Company, LimitedInventors: Hiroshi Kogen, Masaaki Kurabayashi, Teiichiro Koga, Toru Komai, Haruo Iwabuchi
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Patent number: 5594028Abstract: This invention provides certain sulfonamide derivatives, their pharmaceutical formulations, and their use in the treatment of susceptible neoplasms in mammals.Type: GrantFiled: November 21, 1994Date of Patent: January 14, 1997Assignee: Eli Lilly and CompanyInventors: Richard W. Harper, J. Jeffry Howbert, Gerald A. Poore, Brent J. Rieder, Eddie V. P. Tao, James A. Aikins
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Patent number: 5578252Abstract: Described are novel reversible photochromic 3H-naphtho[2,1-b]pyran compounds, examples of which are substituted with an oxy-bearing substituent at the number 8 carbon atom and with either an alkyl group at the number 7 carbon atom or with a carbonyl bearing substituent at the number 9 carbon atom and certain substituents at the 3-position of the pyran ring, e.g., 3,3-spirofluoren-9-ylidene 8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline) type compounds, are also described.Type: GrantFiled: November 29, 1995Date of Patent: November 26, 1996Assignee: Transitions Optical, Inc.Inventors: Barry Van Gemert, Anil Kumar
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Patent number: 5576448Abstract: There are disclosed chemical intermediates of the formula: ##STR1## a salt or a stereochemically isomeric form thereof, wherein: wherein one or two hydrogen atoms in the dihydro-1,4-dioxane moiety may be replaced by a C.sub.1-6 alkyl group;R.sup.1 represents halo; andR.sup.2 represents amino, mono- or di(C.sub.1-6 alkyl)amino, arylC.sub.1-6 alkylamino, or C.sub.1-6 alkylcarbonylamino.Type: GrantFiled: April 3, 1995Date of Patent: November 19, 1996Assignee: Janssen Pharmaceutica N.V.Inventors: Georges H. P. Van Daele, Frans M. A. Van den Keybus
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Patent number: 5569669Abstract: The invention relates to a compound selected from those of formula (I): ##STR1## in which R.sub.1, R.sub.2, R.sub.2', R.sub.2", R.sub.2'", R.sub.3 and n are as defined in the description, an optical isomer, and an addition salt thereof with a pharmaceutically-acceptable acid or base,and medicinal product containing the same useful for treating a mammal afflicted with a disorder associated to 5-HT.sub.1A or 5-HT.sub.2C receptors.Type: GrantFiled: March 10, 1995Date of Patent: October 29, 1996Assignee: Adir et CompagnieInventors: G erald Guillaumet, Marie-Claude Viaud, Pierre Renard, G erard Adam, Daniel-Henri Caignard, B eatrice Guardiola-Lemaitre, Marie-Claire Rettori
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Patent number: 5530028Abstract: Insecticidal compounds having the formula N-(2-R.sup.a -3-R.sup.b -4-R.sup.h -benzoyl)-N'-(2-R.sup.c -3-R.sup.d -4-R.sup.e -5-R.sup.f -benzoyl)-N'-R.sup.g -hydrazine wherein R.sup.a is a halo or lower alkyl; R.sup. b is lower alkoxy, optionally substituted with halo (preferably fluoro); R.sup.c is selected from hydrogen, halo, lower alkyl, lower alkoxy, lower alkoxy lower alkyl, and nitro; R.sup.d, R.sup.e and R.sup.f are each independently selected from hydrogen, bromo, chloro, fluoro, lower alkyl, lower alkoxy, and lower alkoxy lower alkyl; R.sub.g is a (C.sub.4 -C.sub.6)alkyl; R.sup.h is hydrogen, lower alkoxy, lower alkyl, or when taken together with R.sup.b is methylenedioxy (--OCH.sub.2 O--), 1,2-ethylenedioxy (--OCH.sub.2 CH.sub.2 O--), 1,2-ethyleneoxy (--CH.sub.2 CH.sub.2 O--) or 1,3-propyleneoxy (--CH.sub.2 CH.sub.2 CH.sub.2 O--) wherein an oxo atom is located at the R.sup.b position; and the substituents R.sup.c and R.sup.d, or R.sup.d and R.sup.e, or R.sup.e and R.sup.Type: GrantFiled: September 29, 1993Date of Patent: June 25, 1996Assignee: Rohm and Haas CompanyInventors: Zev Lidert, Dat P. Le, Robert E. Hormann, Thomas R. Opie
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Patent number: 5500443Abstract: A compound of formula (I): ##STR1## in which: X represents oxygen or methylene,n represents 1, 2 or 3,R.sub.1 represents hydrogen, aminocarbonyl or hydroxymethyl,R.sub.2 represents: ##STR2## in which R.sub.3 and R.sub.4 are as defined in the description, the isomers thereof and the addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same are useful in the treatment of schizophrenia.Type: GrantFiled: February 22, 1995Date of Patent: March 19, 1996Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Patrick Hautefaye, Olivier Muller, Mark Millan, Mauricette Brocco
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Patent number: 5496847Abstract: Certain aminomethyl-benzodioxanes and benzopyrans are useful serotonergic agents. They possess anxiolytic properties with few of the side effects often associated with dopaminergic agents.Type: GrantFiled: January 24, 1995Date of Patent: March 5, 1996Assignee: Bristol-Myers Squibb Co.Inventors: John D. Catt, Ronald J. Mattson
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Patent number: 5480905Abstract: Compounds represented by the general formula (I): ##STR1## (where R.sub.1 is an admantyl group; R.sub.2 is a hydrogen atom, a lower alkyl group, a lower alkenyl group or an aralkyl group; R.sub.3 is a 1,4-benzodioxane ring that may optionally have 1-4 substituents selected from among a lower alkyl group, a lower alkoxy group, a halogen atom, an amino group, a hydroxyl group and a lower alkylcarbonyl group; n is an integer of 1-4) or a salt thereof. These compounds have both antianxiety and antidepressant actions and yet they cause less side effects. Therefore, they can be used as excellent drugs that are highly effective in the prevention and treatment of various diseases such as neurosis. psychosomatic diseases, autonomic imbalance and depression.Type: GrantFiled: January 6, 1995Date of Patent: January 2, 1996Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Akira Koda, Tatsuo Miyauchi, Yoshitake Kanbe, Hirokazu Hamada
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1,2-ethanediol derivative and salt thereof and cerebral function-improving agent comprising the same
Patent number: 5472984Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.Type: GrantFiled: December 29, 1993Date of Patent: December 5, 1995Assignee: Toyama Chemical Co., Ltd.Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita -
Patent number: 5424456Abstract: New N-Arylalkylderivatives of 2-aminomethyl-2,3-dihydro-1,4-benzodioxine and its (+)- and (-)- enantiomers represented by general formula (I), where R.sub.1, R.sub.2 and R.sub.3 represent H, or R.sub.1 and R.sub.2 represent H and R.sub.3 represent H or R.sub.1 and R.sub.2 represent methoxy and R.sub.3 represents H and their pharmaceutically acceptable organic or inorganic acid addition salts exhibit in pharmacological tests pronounced hypotensive activity as a result of their calcium channel blocking and alpha.sub.1 -adrenergic blocking activity and pronounced antithrombotic action. In a form of pharmaceutical preparations, they are suitable for the treatment and prevention of cardiovascular diseases and other disorders.Type: GrantFiled: November 18, 1993Date of Patent: June 13, 1995Assignee: Vyzkumny Ustav Pro Farmacii A Biochemii s.p.Inventors: Gabriel Butora, Miroslav Rajsner, Ivan Helfert, Vaclav Trcka
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Patent number: 5420132Abstract: A compound of formula (I): ##STR1## wherein: X represents O, S or H.sub.2,R and R' each represents hydrogen or together form a bond,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the description.useful in the treatment or prevention of disorders involving oxidative processes.Type: GrantFiled: May 6, 1994Date of Patent: May 30, 1995Assignee: Adir et CompagnieInventors: Gerald Guillaumet, Gerard Coudert, Valerie Thiery, Gerard Adam, Jean-Guy Bizot-Espiard, Bruno Pfeiffer, Pierre Renard
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Patent number: 5387604Abstract: The present invention is directed to a new class of serotonin 5HT.sub.1A agonists.Type: GrantFiled: October 16, 1992Date of Patent: February 7, 1995Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Ian A. McDonald, Ronald C. Bernotas, Mark W. Dudley, Jeffrey S. Sprouse
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Patent number: 5373023Abstract: The invention provides compounds which are tetrahydronaphthalene derivatives of the formula (I) ##STR1## wherein R.sub.1 represents a halogen atom, a cyano group, a nitro group, an unbranched (C.sub.1 -C.sub.6) alkoxy group, a (C.sub.1 -C.sub.6 cycloalkyl) (C.sub.1 -C.sub.2 alkoxy) group or an aryl (C.sub.1 -C.sub.2 alkoxy) group,R.sub.2 represents a (C.sub.1 -C.sub.4) alkyl group, an aryl group optionally substituted with at least one methoxy group, a pyridyl group or a benzodioxanyl group,R.sub.3 represents a hydrogen atom or a (C.sub.1 -C.sub.2) alkyl group, and n=0 to 3, or are addition salts with pharmaceutically acceptable acids. The compounds of the invention have anti-ischaemic activity.Type: GrantFiled: August 4, 1993Date of Patent: December 13, 1994Assignee: SYNTHELABOInventors: Paul Howard Williams, Christian Hoornaert, Jean Claude Muller
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Patent number: 5312831Abstract: The invention relates to novel ureas and urethanes of Formula I: ##STR1## which stimulate cytokine production and may be used to accelerate recovery from neutropenia accompanying radio- or chemotherapy, bone marrow transplantation, or infections. Compounds in the invention or pharmaceutical compositions employing these compounds may be useful in the treatment of cancer, AIDS, aplastic anemia, myelodysplastic syndrome, and infectious diseases, and in the enhancement of immune response.Type: GrantFiled: May 12, 1993Date of Patent: May 17, 1994Assignee: American Cyanamid CompanyInventors: Semiramis Ayral-Kaloustian, Steven R. Schow, Mila T. Du, James J. Gibbons, Jr.
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Patent number: 5268488Abstract: Disclosed are an acrylate series compound represented by the following formula: ##STR1## wherein R.sup.1 represents a C.sub.1-10 alkoxy group, a halogen atom, a C.sub.1-6 alkyl group, a nitro group, a C.sub.1-6 alkylamino group, a C.sub.1-6 alkylthio group, a halo C.sub.1-6 alkyl group, a pyrrole group, a C.sub.1-6 alkylsulfonyl group, a cyano group, a C.sub.1-6 mono- or dialkylaminosulfonyl group, a phenoxy group which may have a C.sub.1-6 alkoxy group, a benzyloxy group, a halo C.sub.1-6 alkoxy group, a C.sub.3-6 alkenyloxy group, a hydroxyl group, a C.sub.2-7 cyanoalkoxy group, a C.sub.3-6 alkynyloxy group, a C.sub.1-6 alkoxy group substituted by a C.sub.3-6 cycloalkyl group, a C.sub.1-6 alkoxy group substituted by a C.sub.1-6 alkoxy group, a C.sub.2-7 alkoxycarbonyl group or a C.sub.2-7 acyl; R.sup.2 represents a C.sub.3-8 cycloalkyl group which may have a C.sub.1-6 alkyl group; n represents an integer of 0 to 5; a plural number of R.sup.1 s may be the same or different; and when n is 2, two R.sup.Type: GrantFiled: September 11, 1992Date of Patent: December 7, 1993Assignee: Ube Industries, Ltd.Inventors: Masanori Watanabe, Toshinobu Tanaka, Hisato Kobayashi, Shuji Yokoyama, Hideaki Umeyama
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Patent number: 5254595Abstract: Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described.A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.Type: GrantFiled: January 9, 1992Date of Patent: October 19, 1993Assignee: Elf SanofiInventors: Umberto Guzzi, Marco Baroni, Sergio Boveri, Luciano Manara, Alberto Bianchetti
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Patent number: 5252599Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.Type: GrantFiled: August 27, 1992Date of Patent: October 12, 1993Assignee: Merck Frosst Canada, Inc.Inventors: Yves Girard, Rejean Fortin, Daniel Delorme, Daniel Dube, Pierre Hamel, Yves Ducharme, John W. Gillard
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Patent number: 5245051Abstract: A compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are, independently, hydrogen, alkyl, alkoxy, aralkoxy, alkanoyloxy, hydroxy, halo, amino, mono- or dialkylamino, alkanamido or sulfonamido, or R.sup.1 and R.sup.2 together are methylenedioxy, ethylenedioxy, or propylenedioxy; R.sup.3 is hydrogen or alkyl; n is one of the integers 2,3 or 4; X is --C(.dbd.O)-- or --(CH.sub.2).sub.m --, in which m is the integer 0 or 1; Y is methylene, ethylene or ethenylene, or a pharmaceutically acceptable salt thereof, are antipsychotic agents.Type: GrantFiled: September 3, 1992Date of Patent: September 14, 1993Assignee: American Home Products CorporationInventors: Gary P. Stack, Young H. Kang
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Patent number: 5232936Abstract: The present invention relates to novel hydantoin derivatives, processes for producing said hydantoin derivatives, pharmaceutical compositions containing at least one of said hydantoin derivatives as aldose reductase inhibitors and novel intermediate compounds in the synthesis of said hydantoin derivatives.The present invention is based on the selection of a hydantoin which is bonded by a sulfonyl group to various substituents at the 1-position of the hydantoin skeleton.The compounds of the present invention have a strong inhibitory activity against aldose reductase. These compounds are extremely useful for the treatment and/or prevention of various forms of diabetic complications based on the accumulation of polyol metabolites.Type: GrantFiled: January 23, 1991Date of Patent: August 3, 1993Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Ei Mochida, Kimihiro Murakami, Kazuo Kato, Katsuaki Kato, Jun Okuda, Ichitomo Miwa
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Patent number: 5212173Abstract: Pharmacologically active compounds corresponding to the formula I ##STR1## in which n represents 2-5,m represents 2-6,R.sup.1 denotes hydrogen or lower alkyl,R.sup.2 represents an OR.sup.4 group in which R.sup.4 denotes lower alkyl or a phenyl or phenyl-lower alkyl group which is optionally substituted in the phenyl ring, orR.sup.2 represents a ##STR2## group in which R.sup.5 and R.sup.6 independently of one another each denote hydrogen, lower alkyl or a phenyl or phenyl-lower alkyl group which is optionally substituted in the phenyl ring, orR.sup.5 and R.sup.6, together with the nitrogen atom to which they are bonded, represent a saturated 5- or 6-membered heterocycle,R.sup.3 represents a saturated monocyclic or bicyclic hydrocarbon group which is derived from terpenes and has 10 or 11 carbon atoms, andZ represents oxygen or, if R.sup.3 is a dihydronopyl group, Z may also represent sulfur,and salts thereof.Type: GrantFiled: December 19, 1991Date of Patent: May 18, 1993Assignee: Kali-Chemie Pharma GmbHInventors: Herman Kraehling, Samuel David, Insa Hell, Ulf Preuschoff, Ivan Ban, Marie-Odile Christen
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Patent number: 5202351Abstract: A novel 1-phenylalkyl-3-phenylurea derivative represented by the following formula (I): ##STR1## wherein R.sup.1 and R.sup.5 represent independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.5 alkoxyl or halo; R.sup.2 represents hydrogen or C.sub.1 -C.sub.15 alkyl; R.sup.3 represents C.sub.1 -C.sub.15 alkyl or R.sup.3 represents together with R.sup.2 C.sub.2 -C.sub.9 alkylene; R.sup.4 and R.sup.5 represent independently C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxyl or halo; X represents oxygen or sulfur; Y represents --O--(CH.sub.2).sub.l --O-- wherein l is an integer of 1 to 3 or --(CH.sub.2).sub.p -- wherein p is an integer of 3 to 5; m is 0 or an integer of 1 to 5; and n is 0 or an integer of 1 to 3, is provided. The 1-phenylalkyl-3-phenylurea derivative (I) have the action of reducing cholesterol in blood by ACAT inhibition, and therefore, useful for treating hyperlipemia and atherosclerosis.Type: GrantFiled: January 22, 1991Date of Patent: April 13, 1993Assignee: Mitsubishi Kasei CorporationInventors: Tetsuo Sekiya, Shinya Inoue, Chiaki Hyodo, Hiromi Okushima, Kohei Umezu, Kazuo Suzuki
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Patent number: 5189060Abstract: Novel insecticides have the formula ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylthio;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylthio;R.sub.3 is hydrogen, halogen or C.sub.1 -C.sub.4 haloalkyl; orR.sub.1 and R.sub.2 taken together are C.sub.1 -C.sub.4 alkylenedioxy or halo-C.sub.1 -C.sub.3 alkylenedioxy; provided that R.sub.1, R.sub.2 and R.sub.3 are not all hydrogen;R.sub.4 is methyl, ethyl, n-propyl, C.sub.3 -C.sub.7 branched alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.4 alkenyl; or cyclopropyl, optionally substituted by up to 4 methyl groups or up to 2 halogens;R.sub.5 is: ##STR2## R.sub.6 is phenyl, benzyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.3 alkynyl; R.sub.7, R.sub.8, R.sub.10 and R.sub.11 are each halogen; andR.sub.Type: GrantFiled: November 30, 1990Date of Patent: February 23, 1993Assignee: Imperial Chemical Industries PLCInventors: David B. Kanne, Karl J. Fisher, Michael D. Broadhurst
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Patent number: 5168099Abstract: Optically active alkylenedioxybenzene derivatives of the formula: ##STR1## wherein m is an integer of 2-5, and n is an integer of 1-3, and acid addition salts thereof. A pharmaceutical composition containing a compound (I) or racemate, and a method of treating anxiety in a warm-blooded animal by administering the above compound (I) to said animal are also provided.Type: GrantFiled: March 14, 1991Date of Patent: December 1, 1992Assignee: Mitsubishi Kasei CorporationInventors: Heitaro Iwata, Akemichi Baba, Toshio Matsuda, Mitsuo Egawa, Akihiro Tobe, Kenichi Saito
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Patent number: 5153227Abstract: The invention concerns novel pharmaceutical compositions for use in the treatment of certain complications of diabetes and galactosemia and which contain a nitromethane derivative (or its non-toxic salt) as active ingredient. The nitromethane derivatives are inhibitors of the enzyme aldose reductase. Many of the inhibitors are novel and are provided, together with processes for their manufacture and use, as further features of the invention.Type: GrantFiled: February 6, 1989Date of Patent: October 6, 1992Assignee: Imperial Chemical Industries PLCInventors: Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey J. Morris, John Preston
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Patent number: RE35279Abstract: The present invention relates to novel hydantoin derivatives, processes for producing said hydantoin derivatives, pharmaceutical compositions containing at least one of said hydantoin derivatives as aldose reductase inhibitors and novel intermediate compounds in the synthesis of said hydantoin derivatives.The present invention is based on the selection of a hydantoin which is bonded by a sulfonyl group to various substituents at the 1-position of the hydantoin skeleton.The compounds of the present invention have a strong inhibitory activity against aldose reductase. These compounds are extremely useful for the treatment and/or prevention of various forms of diabetic complications based on the accumulation of polyol metabolites.Type: GrantFiled: February 17, 1994Date of Patent: June 18, 1996Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Ei Mochida, Kimihiro Murakami, Kazuo Kato, Katsuaki Kato, Jun Okuda, Ichitomo Miwa