Nitrogen Bonded Directly To Ring Carbon Of The Oxazole Ring Patents (Class 514/377)
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Patent number: 5563159Abstract: There is disclosed a dithiocarbonimide derivative of the formula: ##STR1## wherein B is a C.sub.1 -C.sub.6 alkyl group; X is an NH group or an oxygen atom and Y is a nitrogen atom or a CH group, A is a phenyl group, a heterocyclic group, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a bicycloalkyl group or a tricycloalkyl group, all of which may be substituted. Also disclosed are a fungicidal/insecticidal/acaricidal agent containing the dithiocarbonimide derivative as an active ingredient, an intermediate for use in the production of the dithiocarbonimide derivative, and a process for producing the dithiocarbonimide derivative from the intermediate.Type: GrantFiled: December 2, 1994Date of Patent: October 8, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Tomoyuki Kusaba, Tadashi Ohsumi, Tsuguhiro Katoh, Makoto Fujimura, Norio Kimura, Kazuya Ujihara, Kimitoshi Umeda
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Patent number: 5556855Abstract: 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: GrantFiled: December 29, 1994Date of Patent: September 17, 1996Assignee: Pharmacia ABInventors: Hubert Agback, Leif Ahrgren, Thomas Berglindh, Martin Haraldsson, G oran Smedeg.ang.rd, Lars-Inge Olsson
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Patent number: 5552421Abstract: Various substituted benzoxazoles and benzothiazoles, are described and disclosed, which are potent inhibitors of leukotriene synthesis in warm-blooded animals.Type: GrantFiled: April 6, 1995Date of Patent: September 3, 1996Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.Inventors: Edward S. Lazer, Julian Adams, Clara K. Miao, Peter Farina
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Patent number: 5543433Abstract: 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: GrantFiled: June 3, 1994Date of Patent: August 6, 1996Assignee: BASF AktiengesellschaftInventors: Reinhard Doetzer, Hubert Sauter, Herbert Bayer, Franz Roehl, Gisela Lorenz, Eberhard Ammermann, Horst Wingert
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Patent number: 5541206Abstract: A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed.Type: GrantFiled: April 25, 1995Date of Patent: July 30, 1996Assignee: Abbott LaboratoriesInventors: Dale J. Kempf, Daniel W. Norbeck, Hing Leung Sham, Chen Zhao
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Patent number: 5538991Abstract: Phenoxyphenylacetic acids and derivatives of the general structural formula I ##STR1## have endothelin antagonist activity and are useful in treating cardiovascular disorders, such as hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, benign prostatic hyperplasia, inflammatory diseases including Raynaud's disease and asthma.Type: GrantFiled: September 14, 1994Date of Patent: July 23, 1996Assignee: Merck & Co., Inc.Inventors: Wallace T. Ashton, Linda L. Chang, William J. Greenlee
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Patent number: 5510344Abstract: Compounds of formula I ##STR1## wherein X is oxygen or sulphur, W is CH or N, m is 0 or 1, and either a) n is 1 and Q is a non-aromatic heterocyclic ring of 3 to 10 ring atoms, containing one to three hetero atoms selected from oxygen, sulphur and nitrogen, which may be substituted and may be fused to another ring, with the proviso a) that if Q is thiazol-2-in-2-yl, it is substituted but not by methylene, and b) Q is not a six membered ring containing only two nitrogen atoms, or b) n is 0 or 1 and Q is ##STR2## where R.sup.1 is alkyl, alkoxy or alkylthio, and R.sup.2 is heteroaryl, non aromatic heterocyclyl, optionally substituted cycloalkyl or optionally substituted alkyl containing at least 5 carbon atoms, phenyl substituted by one or more groups selected from halogen, optionally substituted alkyl, alkoxy, haloalkoxy, aryloxy, alkylthio and alkoxycarbonyl, and when R.sup.1 is alkyl or alkoxy, or, when W is nitrogen, R.sup.2 can also be unsubstituted phenyl, have pesticidal especially fungicidal activity.Type: GrantFiled: May 4, 1994Date of Patent: April 23, 1996Assignee: Schering Agrochemicals LimitedInventors: Geoffrey R. Cliff, Ian C. Richards
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Patent number: 5502068Abstract: The invention is directed to novel cyclopropylpyrroloindole-oligopeptide compounds which are useful as anticancer agents. The novel cyclopropylpyrroloindole-oligopeptide compounds have the following general structure: ##STR1## wherein, Het.sup.1 and Het.sup.2 are individually selected from the group consisting of pyrrole, imidazole, triazole, thiophene, furan, thiazole, oxazole and pyrazole,R is selected from the group consisting of a valence bond; a C.sub.1 -C.sub.6 alkyl; a C.sub.2 -C.sub.6 alkenyl; a C.sub.2 -C.sub.6 alkynyl; and an ortho, meta or para linked aromatic group,A is selected from the group consisting of a C.sub.1 -C.sub.6 alkyl group; an amidine or derivative thereof; a guanidine; a secondary, tertiary or quaternary ammonium salt; and a sulfonium salt,n is 0 to 3, andm is 0 to 3.Type: GrantFiled: January 31, 1995Date of Patent: March 26, 1996Assignee: Synphar Laboratories, Inc.Inventors: J. William Lown, Yuqiang Wang, Weide Luo
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Patent number: 5472965Abstract: A novel imidazole derivatives of formula I: ##STR1## wherein R.sup.1 is hydrogen, alkyl, halogen, or optionally substituted aryl; R.sup.2 is alkyl, optionally substituted aryl optionally substituted aralkyl, or optionally substituted hetero ring group; R.sup.3 is hydrogen, alkyl, optionally substituted aryl, optionally substituted aralkyl, or optionally substituted hydroxyalkyl; R.sup.4 is hydrogen, alkyl, halogen, acyl, optionally substituted hydroxyalkyl, optionally esterified or amidated carboxyl group, hydroxy group, aryl or arylthio; X is S, SO, SO.sub.2, CH.sub.2, or Se; n is an integer of 1 to 3, or a pharmaceutically acceptable salt thereof, said derivative having anti-HIV activity and being useful for the treatment of HIV infections.Type: GrantFiled: March 14, 1994Date of Patent: December 5, 1995Assignee: Shionogi & Co., Ltd.Inventors: Hirohiko Sugimoto, Masaru Ogata, Hiroshi Matsumoto, Ken-ichi Sugita, Akihiko Sato, Tamio Fujiwara
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Patent number: 5472976Abstract: This invention relates to polyaminopyrrolecarboxyamide derivatives of general formula (I) and their pharmaceutically acceptable salts, in which A represents a chemical bond or an aromatic or heteroaromatic radical, and:if A is a chemical bond, R is hydrogen, alkyl, dialkylaminoalkyl, alkenyl, cycloalkyl, arylalkyl, arylalkenyl, haloalkyl, or an aromatic or heteroaromatic radical;whereas if A is an aromatic or heteroaromatic radical, R is nitro, amino or formylamino;n is 0 or a whole number between 1 and 4;Z is an alkylene or aromatic radical.Type: GrantFiled: August 6, 1993Date of Patent: December 5, 1995Assignees: A. Menarini Industrie Farmaceutiche Riunite S.r.l., Bristol-Meyers Squibb S.p.A.Inventors: Fabio Animati, Federico Arcamone, Giuseppe Giannini, Paolo Lombardi
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Patent number: 5462946Abstract: The instant invention is directed to the use of a biologically compatible composition, containing an effective amount of a metal independent nitroxide compound which is preferably represented by the formula ##STR1## wherein R.sub.1 is --CH.sub.3 ; R.sub.2 is --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, --C.sub.4 H.sub.9, --C.sub.5 H.sub.11, --C.sub.6 H.sub.13, --CH.sub.2 --CH(CH.sub.3).sub.2, --CHCH.sub.3 C.sub.2 H.sub.5, or --(CH.sub.2).sub.7 --CH.sub.3, or wherein R.sub.1 and R.sub.2 together form spirocyclopentane, spirocyclohexane, spirocycloheptane, spirocyclooctane, 5-cholestane, or norbornane, R.sub.3 is --O. or --OH, or a physiologically acceptable salt thereof, and a pharmaceutically acceptable carrier, as antioxidants capable of protecting cells, tissues, organs, and whole organisms against the deleterious effects of harmful oxygen-derived species generated during oxidative stress.Type: GrantFiled: March 20, 1992Date of Patent: October 31, 1995Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: James B. Mitchell, Amram Samuni, William DeGraff, Stephen Hahn
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Patent number: 5461067Abstract: A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed wherein R.sub.1, R.sub.2, R.sub.5, R.sub.6, Y.sub.m and Y'.sub.n are herein defined.Type: GrantFiled: February 1, 1994Date of Patent: October 24, 1995Assignee: Abbott LaboratoriesInventors: Daniel W. Norbeck, Hing L. Sham, Dale J. Kempf, Chen Zhao
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Patent number: 5436260Abstract: Substituted 1-benzylimidazole-5-methylidene hydantoins are disclosed as well as methods of preparing them, pharmaceutical compositions containing them, and methods of using them. Intermediates useful in the preparation of the compounds of the invention are also disclosed and synthetic methods for preparing the novel intermediates. The compounds are useful as antagonists of angiotensin II and thus are useful in the control of hypertension, hyperaldosteronism, congestive heart failure, surgically induced vascular smooth muscle proliferation, and glaucoma.Type: GrantFiled: January 4, 1994Date of Patent: July 25, 1995Assignee: Warner-Lambert CompanyInventors: John C. Hodges, Sylvester Klutchko
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Patent number: 5413997Abstract: A triphenylmethane derivative represented by the following general formula: ##STR1## exhibits bone absorption inhibiting effects and is useful as a medicament for treating osteoporosis.Type: GrantFiled: January 21, 1993Date of Patent: May 9, 1995Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Iwao Kinoshita, Daisuke Machii, Yasuo Onoda, Haruki Takai, Nobuo Kosaka, Katsuichi Shuto, Katsushige Gomi, Makoto Morimoto, Akio Ishii
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Patent number: 5378715Abstract: Compounds of the formula ##STR1## inhibit endothelin, wherein: one of X and Y is N and the other is O; R is naphthyl or naphthyl substituted with R.sup.1, R.sup.2 and R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 are each independently hydrogen; alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, or aralkyl, any of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3 ; halo; hydroxyl; cyano; nitro; --C(O)H; --C(O)R.sup.6 ; CO.sub.2 H; --CO.sub.2 R.sup.6 ; --SH; --S(O).sub.n R.sup.6 ; --S(O).sub.m --OH; --S(O).sub.m --OR.sup.6 ; --O--S(O).sub.m --R.sup.6 ; --O--S(O).sub.m OH; --O--S(O).sub.m --OR.sup.6 ; --Z.sup.4 --NR.sup.7 R.sup.8 ; or --Z.sup.4 --N(R.sup.11)--Z.sup.5 --NR.sup.9 R.sup.10 ;R.sup.4 and R.sup.5 are each independently hydrogen; alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, or aralkyl, any of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.Type: GrantFiled: July 15, 1993Date of Patent: January 3, 1995Assignee: Bristol-Myers Squibb Co.Inventors: Philip D. Stein, John T. Hunt, Natesan Murugesan
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Patent number: 5340832Abstract: A novel prolinal derivative of the general formula: ##STR1## [wherein A represents alkylene or alkenylene group of from 1 to 8 carbon atom(s) or a saturated hydrocarbon ring of from 3 to 7 carbon atoms, R represents hydrogen atom, phenyl group, benzyl group, alkyl group of from 1 to 8 carbon atom(s) or cycloalkyl group of from 3 to 7 carbon atoms,B represents alkylene group of from 1 to 8 atom(s) unsubstituted or substituted by phenyl group or benzyl group, or a single bond,D represents carbocyclic or heterocyclic ring unsubstituted or substituted by from one to three of halogen atom, alkyl or alkoxy group of from 1 to 4 carbon atom(s), nitro group or trifluoromethyl group.]possess inhibitory activity on prolyl endopeptidase, and therefore are useful for treating and/or preventing agent as a amnesia.Type: GrantFiled: August 17, 1993Date of Patent: August 23, 1994Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
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Patent number: 5334614Abstract: The invention concerns hydroxylamine derivatives of the formula I ##STR1## wherein R.sup.4 is hydrogen, carbamoyl, (1-4C)alkyl, cyclopentyl, cyclohexyl, tetrahydrofuran-3-yl, tetrahydropyran-4-yl, piperidin-4-yl, N-(1-4C)alkylpiperidin-4-yl, (2-5C)alkanoyl, (1-4C)alkylsulphonyl, N-(1-4C)alkylcarbamoyl, N,N-di-(1-4C)alkylcarbamoyl, phenyl, phenyl-(1-4C)alkyl, di-phenyl-(1-4C)alkyl, benzoyl, phenylsulphonyl or a heteroarylmethyl group;R.sup.5 is hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl;A.sup.4 is (1-4C)alkylene;Ar.sup.1 is phenylene, pyridinediyl or pyrimidinediyl;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl or thiazolediyl;R.sup.1 is hydrogen, (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula -A.sup.2 -X.sup.2 -A.sup.3 -wherein each of A.sup.2 and A.sup.Type: GrantFiled: May 11, 1993Date of Patent: August 2, 1994Assignees: Zeneca Ltd., Zeneca Pharma SAInventors: Philip N. Edwards, Michael S. Large
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Patent number: 5332757Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene or a heteroaryl diradical;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula -A.sup.2 -X.sup.2 -A.sup.3 - which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.Type: GrantFiled: February 8, 1993Date of Patent: July 26, 1994Assignees: Zeneca Limited, Zeneca PHARMA S AInventors: Thomas G. C. Bird, Patrick Ple
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Patent number: 5324723Abstract: 1,3-Oxazole and 1,3-thiazole compounds of formula I, and their pharmaceutically acceptable salts and prodrugs: ##STR1## wherein X represents oxygen or sulphur;R.sup.1 represents a non-aromatic azacyclic or azabicyclic ring system.Type: GrantFiled: July 1, 1993Date of Patent: June 28, 1994Assignee: Merck Sharpe & Dohme Ltd.Inventors: Raymond Baker, John Saunders, Roger J. Snow, Graham A. Showell
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Patent number: 5314889Abstract: A 2-Acylaminothiazole of formula: ##STR1## in which R.sub.1 is H, an alkyl or a substituted alkyl; R.sub.IV is a cycloalkyl, an aromatic group such as phenyl or a heterocyclic group which are unsubstituted or substituted; R.sub.V is a substituted alkyl, a substituted carboxy such as an ester or an amide; or R.sub.IV and R.sub.V together represent a phenoxyalkylene group which may be substituted on the phenyl; and Z is a heterocyclic e.g. indolyl group; or a salt of compound (I).Type: GrantFiled: May 29, 1992Date of Patent: May 24, 1994Assignee: Elf SanofiInventors: Robert Boigegrain, Roger Brodin, Danielle Gully, Jean-Charles Molimard, Dominique Olliero
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Patent number: 5294616Abstract: A series of non-peptide derivatives that are antagonists of the fibrinogen IIb/IIIa receptor and thus are platelet aggregation compounds useful in the prevention and treatment of diseases caused by thrombus formation.Type: GrantFiled: March 25, 1992Date of Patent: March 15, 1994Assignee: Merck & Co., Inc.Inventors: Mark E. Duggan, Melissa S. Egbertson, Wasyl Halczenko, George D. Hartman, Laura M. Turchi, William L. Laswell
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Patent number: 5290802Abstract: This invention relates to novel 3-substituted-2-oxindole derivatives which are inhibitors of prostaglandin H.sub.2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H.sub.2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H.sub.2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.Type: GrantFiled: June 5, 1991Date of Patent: March 1, 1994Assignee: Pfizer Inc.Inventors: Frederick J. Ehrgott, Carl J. Goddard, Gary R. Schulte
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Patent number: 5288732Abstract: Novel fungicides of the formula ##STR1## in which R.sup.1 represents optionally substituted hydroxyalkyl, optionally substituted hydroxyalkoxyalkyl, optionally substituted heteroarylalkyl or optionally substituted heteroaryl, andR.sup.2 represents optionally substituted alkyl, optionally substituted alkenyl, or alkinyl.Intermediates therefor, wherein R.sup.2 is hydrogen or an alkali metal cation, are also new.Type: GrantFiled: March 31, 1993Date of Patent: February 22, 1994Assignee: Bayer AktiengesellschaftInventors: Herbert Gayer, Klaus Jelich, Winfried Lunkenheimer, Wilhelm Brandes, Gerd Hanssler
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Patent number: 5272167Abstract: Compounds of the formulaZ--X--Q--Y--Wpharmaceutically acceptable acid addition, basic addition salts or quaternary amine salts thereof, whereinZ is phenyl, substituted phenyl, wherein the substituents are independently one or more of halogen, lower alkylthio, loweralkylsulfonyl, lower alkoxy, oxazol-2-yl; imidazo-1-yl; lower alkyl substituted imidazo-1-yl; or tert-butyl;X is a bond, ##STR1## Q is lower alkane-diyl or 5, 6, or 7 carbon atoms optionally substituted by --OH; loweralkylnediyl of 6-8 carbon atoms; methylcyclohexylmethyl; tetrahydrofurandiyl; or (C.sub.1 -C.sub.2) lower alkane-diyl tetrahydrofurandiyl-C.sub.1 -C.sub.2 loweralkanediyl; wherein the tetrahydrofuran ring is substituted by 0-2 hydroxy groups;Y is a bond; andW is benzimidazol-1-yl or benzimidazol-2-yl are described. These compounds have antiviral activity, antiinflammatory activity and are PAF inhibitors.Type: GrantFiled: December 18, 1991Date of Patent: December 21, 1993Assignee: Schering CorporationInventors: Viyyoor M. Girijavallabhan, Ashit K. Ganguly, Patrick A. Pinto, Richard W. Versace
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Patent number: 5240950Abstract: There are provided carbazate derivatives of the formula:R.sup.1 --N.dbd.CH--NHNH--R.sup.2wherein R.sup.1 is a heterocyclic group; and R.sup.2 is an esterified carboxyl group, and their salts, which are useful as AGE-formation inhibitory agents.The derivatives or the salts can be produced by reacting compounds of the formula: R.sup.1 --N.dbd.CH--OR.sup.3 wherein R.sup.1 is a heterocyclic group; and R.sup.3 is a lower alkyl group, with a carbazic acid ester or its salt.Type: GrantFiled: September 7, 1989Date of Patent: August 31, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Takashi Sohda, Hitoshi Ikeda, Yu Momose
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Patent number: 5234917Abstract: Angiotensin II receptor antagonists having the formula: ##STR1## which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mammals.Type: GrantFiled: November 30, 1990Date of Patent: August 10, 1993Inventors: Joseph A. Finkelstein, Judith Hempel, Richard M. Keenan, James Samanen, Joseph Weinstock
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Patent number: 5223517Abstract: Heterocyclically substituted cycloalkano[b]-indolesulphonamides can be prepared by reaction of appropriate N-unsubstituted indoles with acrylonitrile, followed by hydrolysis, esterification or amidation, or by reaction of heterocyclically substituted hydrazines with cycloalkanones or by subsequent introduction of the heterocyclic group into appropriate indole derivatives. The heterocyclically substituted cycloalkano[b]-indolesulphonamides can be employed for the treatment of thromboembolic disorders, ischaemias, arteriosclerosis, asthma, allergies and for the prophylaxis of myocardial infarcts.Type: GrantFiled: August 23, 1991Date of Patent: June 29, 1993Assignee: Bayer AktiengesellschaftInventors: Ulrich E. Muller, Ulrich Niewohner, Elisabeth Perzborn, Erwin Bischoff, Hans-Georg Dellweg
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Patent number: 5206253Abstract: The present invention concerns novel disphosphonates having the general formula I ##STR1## in which Het represents a heterocyclic five-membered ring with 2-4 heteroatoms which is substituted, if desired, and which can also be partially hydrogenated,R.sub.1 -R.sub.7 each denote, independently of each other, hydrogen or C.sub.1 -C.sub.5 alkyl,X=denotes hydrogen, OH or the group --NR.sub.8 R.sub.9, in which R.sub.8 and R.sub.9 should each be, independently of each other, hydrogen or C.sub.1 -C.sub.5 alkyl,m and n denote, independently of each other, 0, 1 or 2,as well as their pharmacologically safe salts and optically active forms.Type: GrantFiled: November 25, 1991Date of Patent: April 27, 1993Assignee: Boehringer Mannheim, GmbHInventors: Elmar Bosies, Frieder Bauss
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Patent number: 5202340Abstract: The compounds of the formula: ##STR1## (wherein R.sup.1 is hydrogen or alkyl; R.sup.2 is carbocyclic or heterocyclic ring, unsubstituted or substituted by R.sup.3 s; R.sup.3 is halogen, trihalomethyl, hydroxy, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfornyl, cyano, nitro, or group of the formula: --C.sub.6 H.sub.4 --R.sup.4, --NR.sup.5 R.sup.6, --CO--R.sup.7, --COOR.sup.8, --CONR.sup.5 R.sup.6, --SO.sub.2 NR.sup.5 R.sup.6 or --NHCO--R.sup.7, in which R.sup.4 is hydrogen, halogen, trihalomethyl, hydroxy, alkyl or alkoxy, R.sup.5 and R.sup.6 are each hydrogen or alkyl, R.sup.7 is alkyl or phenyl substituted by R.sup.4 and R.sup.8 is hydrogen or alkyl; Z is hydrogen or group of the formula: --COR.sup.9, ##STR2## in which R.sup.9 is alkyl or phenyl substituted by R.sup.10, in which R.sup.10 is hydrogen, halogen, trihalomethyl, alkyl or alkoxy, R.sup.11 and R.sup.12 are each hydrogen, alkyl or phenyl substituted by R.sup.10, or R.sup.11 and R.sup.Type: GrantFiled: April 2, 1991Date of Patent: April 13, 1993Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masanori Kawamura, Yoshinobu Arai, Hideki Aishita
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Patent number: 5192782Abstract: This invention relates to compounds of Formula I and the stereoisomers and pharmaceutically acceptable salts thereof ##STR1## wherein R is alkyl, alkenyl, alkynyl, or (CH.sub.2).sub.m R.sup.3 whereR.sup.3 is cycloalkyl and m is 1 or 2;R.sup.1 is alkyl;R.sup.2 is hydrogen or alkyl;R.sup.4 is alkyl;n is an integer from 1 to 5;p is an integer from 0 to 6;Y is oxygen; andZ is hydrogen, alkyl, alkoxy, NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen or alkyl, or SR.sup.6 wherein R.sup.6 is hydrogen, benzyl or alkyl.The compounds of Formula I are leukotriene B.sub.4 antagonists and are useful as anti-inflammatory agents and in the treatment of leukotriene B.sub.4 mediated conditions.Type: GrantFiled: September 13, 1991Date of Patent: March 9, 1993Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Thomas D. Penning, James P. Snyder
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Patent number: 5185353Abstract: A method for killing or controlling nematode pests which comprises applying to the locus of the pests or to a plant susceptible to attack by the pest an effective amount of a compound of formula (I): ##STR1## wherein R.sup.1 is an optionally substituted aryl or optionally substituted heterocyclic group and novel compounds of formula (I) where R.sup.1 is not phenyl.Type: GrantFiled: November 8, 1990Date of Patent: February 9, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael D. Turnbull, Robert W. Parsons, Andrew D. S. Watkins
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Patent number: 5180731Abstract: A compound of the formula: ##STR1## wherein A is the group of the formula:Ar.sup.1 --D--Ar.sup.2 --wherein Ar.sup.1 is a phenyl or thienyl group which may be optionally substituted with at least one of the same or different halogen atom; Ar.sup.2 is a phenylene or thienylene group which may be optionally substituted with at least one of the same or different halogen atom; D is a divalent radical selected from the group consisting of >C.dbd.N--OR .sup.4 [wherein R.sup.4 is a hydrogen atom or lower alkyl group], >C.dbd.O, ##STR2## >CHOH, >NH radical, or single bond, ##STR3## wherein R.sup.5 is a lower alkoxy or phenyl group which may be optionally substituted with at least one of the same or different halogen atom; E is a methine group or a nitrogen atom; F is a vinylene group or an oxygen atom, ##STR4## wherein R.sup.6 is a lower alkoxy group; R.sup.7 is a lower alkyl group; R.sup.Type: GrantFiled: July 18, 1991Date of Patent: January 19, 1993Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Yukinori Ozato, Nobuhiko Tamura, Hiroaki Masumori, Michihiro Yamamoto, Atsuyuki Kojima, Fumio Nishikaku, Yoshihiko Kimura
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Patent number: 5151440Abstract: A pharmaceutical composition, preferably ophthalmic solution or ophthalmic suspension, useful for treating animals of the mammalian species, including humans, to reduce or maintain intraocular pressure in the eye contains as its pharmacologically active ingredient one or more compounds of the formula ##STR1## where X is O, S or NH; n is an integer with the values of 0, 1 or 2; when n is 0 then R.sub.1 is lower alkyl having 1 to 6 carbon atoms and R.sub.2 is H or lower alkyl having 1 to 6 carbon atoms; when n is 1 or 2, then R.sub.1 and R.sub.2 are methylene (CH.sub.2), or methylene substituted with an R.sub.5 group where R.sub.5 is lower alkyl of 1 to 6 carbons; R.sub.3 and R.sub.4 independently are H or lower alkyl having 1 to 6 carbons; R.sub.6 is H or lower alkyl of 1 to 6 carbons.Type: GrantFiled: February 28, 1990Date of Patent: September 29, 1992Assignee: Allergan, Inc.Inventor: Charles Gluchowski
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Patent number: 5116857Abstract: The present invention relates to the use of substituted benzamides of formula (1): ##STR1## in which: A is linear or branched C.sub.1 -C.sub.3 alkyl; allyl or diethylaminoethyl;R.sub.1 is hydrogen or methyl, andZ-- is --NH--, --O-- or --S--,and of their pharmacologically acceptable salts for modifying gastric motility.Type: GrantFiled: December 14, 1989Date of Patent: May 26, 1992Assignee: Laboratoires Delagrange Div. Societe d'Applications PharmacodynamiquesInventors: Jacques Acher, Jean-Claude Monier, Jean-Paul Schmitt, Brenda Costall, Robert Naylor, Renee Gardaix-Luthereau
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Patent number: 5114959Abstract: Fungicidal substituted acrylic esters of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or alkenyl, or represents in each case optionally substitued aralkyl, aralkenyl, aryl or heteroaryl,R.sup.2 represents halogen, cyano, nitro, formyl, halogenoalkyl, alkoxyalkyl or alkylthioalkyl, or represents hydroximinoalkyl, alkoximinoalkyl, N-alkyliminoalkyl, N-aryliminoalkyl or N,N-dialkylhydrazonoalkyl, or represents alkoxy, alkylthio, halogenoalkoxy or halogenoalkylthio, or represents aryloxy or arylthio, or represents alkanoyl, alkoxycarbonyl, N,N-dialkylcarbamoyl or heterocyclylcarbonyl,R.sup.3 represents alkyl, or represents optionally substituted aralkyl,R.sup.4 represents dialkylamino or represents a radical --Z--R.sup.5,X represents oxygen or sulphur andY represents oxygen or sulphur or represents a radical ##STR2## where R.sup.5 represents alkyl or represents optionally substituted aralkyl,R.sup.Type: GrantFiled: February 9, 1990Date of Patent: May 19, 1992Assignee: Bayer AktiengesellschaftInventors: Alexander Klausener, Gerd Kleefeld, Wilhelm Brandes, Stefan Dutzmann, Gerd Hanssler
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Patent number: 5112841Abstract: Described herein are imidazole derivatives having a specific structure and satisfactory as antiepileptics from the standpoint of the strength of action, prolonged action and side effects as well as their preparation processes.Type: GrantFiled: February 28, 1991Date of Patent: May 12, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Akira Matsubara, Kazuya Sakai, Hideki Tanada, Akira Mizuchi, Kazutoshi Horikomi, Takuma Ohtsu
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Patent number: 5110824Abstract: The invention relates to the use of benzamide derivatives of the formula: ##STR1## in which: A is a diethylaminoethyl group or a group of the formula II: ##STR2## where R is a C.sub.1 -C.sub.3 alkyl, allyl, cyclopropylmethyl or cyclohexenylmethyl group,X is a chlorine or bromine atom, andZ is --NH-- or --O-- with the following condition: when Z is --O--, A is a diethylaminoethyl group, and their pharmacologically acceptable salts for the preparation of medicinal products which are useful in the treatment and prevention of disorders of the cognitive function.Type: GrantFiled: April 12, 1990Date of Patent: May 5, 1992Assignee: Societe d'Etudes Scientifiques et Industrielles de L'Ile-de-FranceInventors: Jacques Acher, Jean-Claude Monier, Jean-Paul Schmitt, Renee Gardaix-Luthereau, Brenda Costall, Robert Naylor
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Patent number: 5096914Abstract: Benzopyran derivatives of the general formula I ##STR1## wherein the substituents are as defined herein are provided. The compounds show vasodilating and vascular spasmolytic activity and are useful in treating hypertension.Type: GrantFiled: November 30, 1990Date of Patent: March 17, 1992Assignee: Beiersdorf AktiengesellschaftInventors: Wolfgang Stenzel, Theo Schotten, Ben Armah
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Patent number: 5086066Abstract: The present invention relates to the application of substituted benzamides of formula (I): ##STR1## in which: A is diethylaminoethyl, 1-ethyl-2-pyrrolidinylmethyl or 1-allyl-2-pyrrolidinylmethyl;R.sub.1 is hydrogen or methyl;X is chlorine or bromine;Z is --NH-- or --O-- except when Z is --NH--,R.sub.1 is hydrogen and X is chlorine, and of their pharmacologically acceptable addition salts, as anxiolytics and antipsychotics.Type: GrantFiled: December 20, 1989Date of Patent: February 4, 1992Assignee: Laboratoires Delagrange Societe d'Applications PharmacodnymiquesInventors: Jacques Acher, Jean-Claude Monier, Jean-Paul Schmitt, Renee Gardaix-Luthereau, Robert Naylor, Brenda Costall
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Patent number: 5081137Abstract: The present invention concerns amino-2 aryloxymethyl-5 oxazolines having the structure: ##STR1## wherein the aryl group Ar is choosen from the group consisting in phenyl-2 phenyl, phenyl-3 and phenyl-4 phenyl. The compounds according to the invention are useful as medicines.Type: GrantFiled: April 11, 1990Date of Patent: January 14, 1992Assignee: Laboratoires SARGETInventors: Patrick Descas, Emmanuel Panconi, Christian Jarry
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Patent number: 5071841Abstract: The present invention provides a sulfur-containing heterocyclic compound of the formula (I) ##STR1## wherein ring A is a benzene ring which may be substituted; R is a hydrogen atom or a hydrocarbon group which may be substituted; B is a carboxyl group which may be esterified or amidated; X is --CH(OH)-- or --CO--; k is 0 or 1; and k' is 0, 1 or 2 or a pharmaceutically acceptable salt thereof.Also, it provides a process for producing the compound (I) or a salt thereof and a pharmaceutical preparation for use in the treatment of osteoporosis comprising the compound (I) or salt thereof.The compounds (I) and salts thereof show excellent bone resorption inhibitory activity.Type: GrantFiled: December 28, 1989Date of Patent: December 10, 1991Assignee: Takeda Chemical Industries, Ltd.Inventors: Takashi Sohda, Masao Tsuda, Iwao Yamazaki
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Patent number: 5066664Abstract: Compounds of the formula ##STR1## where X is O or S; R.sub.1 is lower alkyl having 1 to 6 carbons; R.sub.2 is H, lower alkyl having 1 to 6 carbons; or OR.sub.2.sup.* where R.sub.2.sup.* is lower alkyl having 1 to 6 carbons; Y is O, S or NH; and R.sub.3 is H, lower alkyl having 1 to six carbons, or C(O)R.sub.3.sup.* where R.sub.3.sup.* is lower alkyl having 1 to 5 carbons, with the proviso that the YR.sub.3 group is not disposed in the ortho position on the benzene nucleus relative to the 2-amino group of the oxazoline or thiazoline heterocycle, are active in maintaining or reducing intraocular pressure in the mammalian eye, and are active as vasoconstrictors and capable of reducing or controlling intraocular bleeding of the mammalian eye.Type: GrantFiled: February 28, 1990Date of Patent: November 19, 1991Assignee: Allergan, Inc.Inventor: Charles Gluchowski
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Patent number: 5064827Abstract: Compounds of the present invention, are represented by the general formula ##STR1## wherein R.sub.1 group which may be alkyl of from 1 to about 6 carbon atoms, alkenyl of from 2 to about 6 carbon atoms, alkynyl of from 2 to about 10 carbon atoms, alkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms, halogen, acetamido, amino, nitro, alkylamino of from 1 to about 6 carbon atoms, hydroxy, hydroxyalkyl of from 1 to about 6 carbon atoms, cyano or arylalkoxy wherein the alkyl group contains from 1 to about 6 carbon atoms R.sub.2, R.sub.3 and R.sub.4 are hydrogen or hydroxyl groups or the combination of either hydrogen or hydroxyl groups; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NHCOR.sub.5, --NHCONR.sub.5 R.sub.6, or --NHCOOR.sub.5 wherein R.sub.5 and R.sub.Type: GrantFiled: August 23, 1990Date of Patent: November 12, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Ghanshyam Patil, William L. Matier, Khuong H. X. Mai
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Patent number: 5059620Abstract: The present invention relates to new compounds of the formula ##STR1## wherein X is ##STR2## wherein R.sub.1 is hydrogen, lower alkyl, phenyl, benzyl, cinnamoyl, thiophene, furan, pyrrole, imidazole, pyrazole oxazole or thiazole; W is hydrogen or hydroxy; (Y).sub.A is positioned ortho to W and is an aminoloweralkyl having the formula --CH.sub.2 NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 are the same or different and may be lower alkyl or R.sub.2 and R.sub.3 may together with N form a pyrrolidine, piperidine or azepine ring, and A is 2; n and m are independently from 0 to 5; and R is straight or branched C.sub.1 -C.sub.10 alkyl, straight or branched C.sub.3 -C.sub.10 cycloalkyl, straight or branched C.sub.2 -C.sub.4 alkenyl or straight or branched C.sub.2 -C.sub.4 alkynyl, or a pharmaceutically acceptable salt thereof.These compounds are useful in the treatment of various cardiac arrhythmias.Type: GrantFiled: April 7, 1988Date of Patent: October 22, 1991Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: David M. Stout, William L. Matier, Lawrence A. Black
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Patent number: 5051421Abstract: Benzo[b]thiophene derivatives of formula ##STR1## their tautomers and salts, in which the index n is 0, 1 or 2, alk is lower alkylene, Ar is phenyl, naphthyl or a monocyclic, five- or six-membered heteroaryl radical, wherein the aromatic radical is unsubstituted or is mono- or poly-substituted by lower alkyl, halo-lower alkyl, halogen and/or by nitro, and the ring A is unsubstituted or is mono- or poly-substituted by lower alkyl, lower alkoxy, lower alkylthio, lower alkanesulfinyl, lower alkanesulfonyl, halo-lower alkyl, halogen and/or by nitro, can be used, for example, as active ingredients in medicaments.Type: GrantFiled: January 18, 1990Date of Patent: September 24, 1991Assignee: Ciba-Geigy CorporationInventor: Pier G. Ferrini
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Patent number: 5034406Abstract: A method of reducing or maintaining intraocular pressure in a mammalian eye, e.g., affected with glaucoma, is disclosed. This method comprises administering directly to the mammalian eye an effective amount of one or more 2-cycloalkylamino oxazolines, salts thereof, bases thereof and mixtures thereof.Type: GrantFiled: September 26, 1989Date of Patent: July 23, 1991Assignee: Allergan, Inc.Inventor: Charles Gluchowski
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Patent number: 5032591Abstract: A pharmaceutical product comprising a potassium channel activator antihypertensive agent and a .beta.-blocker antihypertensive agent as a combined preparation for simultaneous, separate or sequential use in therapy of hypertension.Type: GrantFiled: January 4, 1989Date of Patent: July 16, 1991Assignee: Beecham Group p.l.c.Inventors: John M. Evans, Robin E. Buckingham
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Patent number: 5030629Abstract: A method and compositions for enhancing absorption of topically administered physiologically active agents through the skin and mucous membranes of humans and animals in a transdermal device or formulation for local or systemic use, comprising a therapeutically effective amount of a pharmaceutically active agent and a non-toxic, effective amount of penetration enhancing agent of the formula I: ##STR1## wherein R is a saturated or unsaturated, straight or branched, cyclic or acyclic hydrocarbon group with from 1 to 19 carbon atoms, alkoxyalkyl, haloalkyl, specifically trifluoromethyl, alkoxy, amino, alkylamino and acylamino; R' and R" are hydrogen, alkyl, trifluoromethyl, alkoxyalkyl, aminoalkyl, alkyl- and acylaminoalkyl, carboxy, carbalkoxy, hydroxyalkyl or lower alkyl ester thereof; X is O or NR.sub.1 wherein R.sub.Type: GrantFiled: August 11, 1989Date of Patent: July 9, 1991Inventor: Vithal J. Rajadhyaksha
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Patent number: 5011849Abstract: Ethylenediamine monoamides of the formulaR--CO--NH--CH.sub.2 --CH.sub.2 --NH.sub.2 Iwherein R is one of groups ##STR1## in which R.sup.1 is phenyl monohalophenyl, monolower-alkylphenyl, monolower-alkoxypheynl, monotrifluoromethylphenyl, monocyanophenyl or monoaryl-lower-alkoxyphenyl, dihalophenyl, furyl, thienyl or monohalothienyl, R.sup.2 is hydrogen, halogen or amino, R.sup.3, R.sup.5 and R.sup.7 each are phenyl, monohalophenyl, dihalophenyl, thienyl, furyl or monohalofuryl, R.sup.4 and R.sup.6 each are hydrogen or amino and R.sup.8 is hydrogen or lower-alkyl, as well as their pharmaceutically usable acid addition salts are disclosed. The compounds have monoamine oxidase inhibiting properties with low toxicity and are useful for the treatment of depressive states and cognitive disorders.Type: GrantFiled: July 21, 1989Date of Patent: April 30, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Walter Gassner, Rene Imhof, Emilio Kyburz
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Patent number: 5010093Abstract: The invention relates to a nitric ester derivative with vasodilating properties for treatment of cardiovascular disorders, the derivative being of the formula ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, halo(lower)alkyl, halogen, phenyl, nitrophenyl, pyridyl, morpholino, piperidino, amino, lower alkanoylamino, higher alkanoylamino, benzamido, lower alkoxycarbonylamino, N-lower alkylamino, N,N-di(lower)alkylamino, N-lower alkyl-N-lower alkanoylamino, 3-lower alkylureido or N,N-di(lower) alkylamino(lower)alkyl,R.sup.2 is hydrogen, lower alkyl or N-(nitrooxy(lower)alkyl)carbamoyl,Y is a single bond, lower alkylene or lower alkenylene, andZ is ethylene, trimethylene, tetramethylene, 1-methylnitrooxymethylethylene, 1,1-bis(nitrooxy-methyl)ethylene, 2-nitrooxytrimethylene or ethyleneoxyethylene, and pharmaceutically acceptable salts thereof.Type: GrantFiled: March 16, 1990Date of Patent: April 23, 1991Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Youichi Shiokawa, Koichi Takimoto, Kohei Takenaka