Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Hetero Ring Patents (Class 549/468)
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Patent number: 5596100Abstract: A method is provided for the regioselective, palladium catalyzed carbo- or heteroannulation of internal alkynes by aryl iodides containing o-substituted side chains to yield aromatic carbocyclic and heterocyclic ring systems.Type: GrantFiled: April 4, 1995Date of Patent: January 21, 1997Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 5567728Abstract: Use of a compound selected from the group consisting of 3,5-diiodo-4-(2-N, N-diethylaminoethoxy)phenyl-(2-butylbenzofur-3-yl)methanol hydrochloride (001), 2-methyl-3-(3,5-diiodo-4-(2-N,N-diethylaminoethoxy)-benzoyl)benzofuran hydrochloride (003), 2-n-butyl-3-(3,5-diiodo-4-carboxymethoxybenzoyl)benzofuran (005), 2-methyl-3-(3,5-diiodo-4-hydroxy-benzoyl)benzofuran (011), 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (015), 4'-hydroxy-3'-iodo-3,5-diiodo-4-(2-N,N-diethylaminoethoxy)benzophenon hydrochloride (024), 2-butyl-3-(3-iodo-4-hydroxy-benzoyl)benzofuran (029), 4'4'-dihydroxy-3'3,5-triiododiphenylmethan (032), which compound is a 3,5,3'-triiodothyronine (T-3) receptor ligand, for the preparation of a medicament for the therapeutic or prophylactic treatment of a disorder which depends on the expression of T-3 regulated genes, and pharmaceutical preparations comprising said compounds, are disclosed.Type: GrantFiled: February 25, 1994Date of Patent: October 22, 1996Assignee: Karobio AktiebolagInventors: Ulf Norinder, Jurgen Bajorath, Jay F. Stearns
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Patent number: 5565488Abstract: The inventive Oxalylamino-benzofuran- and benzothienyl-derivatives are prepared by reacting the appropriate amino substituted benzofuranes and benzothiophenes with oxalic acid derivatives. The inventive compounds are suitable for the prevention and treatment of acute and chronic inflammatory processes, particularly of the airways.Type: GrantFiled: May 23, 1995Date of Patent: October 15, 1996Assignee: Bayer AktiengesellschaftInventors: Gabriele Braunlich, Rudiger Fischer, Mazen Es-Sayed, Rudolf Hanko, Stephen Tudhope, Graham Sturton, Trevor Abram, Wendy J. McDonald-Gibson, Mary F. Fitzgerald
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Patent number: 5504213Abstract: The Benzofuranyl- and -thiophenyl-alkane-carboxylic acid derivatives are prepared Tby cyclisation of hydroxy acetophenones and related compounds or by Wittig-reaction of benzofuranyl aldehydes. The compounds can be used to prepared medicaments.Type: GrantFiled: April 29, 1994Date of Patent: April 2, 1996Assignee: Bayer AktiengesellschaftInventors: Rudiger Fischer, Gabriele Braunlich, Klaus-Helmut Mohrs, Rudolf Hanko, John-Edward Butler-Ransohoff, Mazen Es-Sayed, Graham Sturton, Steve Tudhope, Trevor Abram, Wendy J. McDonald-Gibson
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Patent number: 5480645Abstract: Hydroxyamines N-acyl derivatives with benzochroman or 2,3-dihydrobenzofuran carboxy acids and relative pharmaceutical composition for the therapeutic treatment of those CNS, vascular, cardiovascular, dermatologic and ophthalmic pathologies wherein it is important to associate an inflammatory modulation effect to an antioxidant activity.Type: GrantFiled: December 29, 1993Date of Patent: January 2, 1996Assignee: LifeGroup S.p.A.Inventors: Francesco Della Valle, Silvana Lorenzi, Gabriele Marcolongo
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Patent number: 5470999Abstract: Compounds of Formula 1 ##STR1## where R.sub.1 -R.sub.5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.Type: GrantFiled: December 30, 1993Date of Patent: November 28, 1995Assignee: Allergan, Inc.Inventor: Roshantha A. Chandraratna
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Patent number: 5455265Abstract: Process of treatment of mammals, including humans to treat diseases or conditions of the type which are normally treated with retinoid-like compounds is disclosed, with pharmaceutical compositions containing an active compound which is a selective agonist of the RXR retinoid receptor sites in preference to the RAR retinoid receptor sites. A compound is defined to be a selective agonist of the RXR receptor site if the compound is at least approximately ten times more effective as an agonist in the RXR receptor sites than in the RAR receptor sites.Type: GrantFiled: February 11, 1993Date of Patent: October 3, 1995Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5440054Abstract: Described is a novel compound and method, useful for treatment of cardiac arrhythmias, especially useful in patients with congestive heart failure (CHF). A process for synthesizing the novel compound is also described.Type: GrantFiled: June 16, 1994Date of Patent: August 8, 1995Assignee: Advanced Therapies, Inc.Inventor: Pascal Druzgala
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Patent number: 5432195Abstract: The present invention relates to a compound expressed by the following general formula (I), pharmacologically-acceptable salt thereof and pharmaceutical composition mainly comprising the same. ##STR1## wherein R.sup.1 is hydrogen, halogen or alkyl; R.sup.2 is alkoxycarbonyl, aralkyloxycarbonyl, carboxy, hydroxyalkyl or acyloxyalkyl; Y is >CHOH, >CHOZ, >CH.sub.2 or >CO; and Z is acyl.The pharmaceutical composition of the present invention is effective for prevention and therapy of arteriosclerosis, ischemic heart diseases, cerebral infarction and restenosis after PTCA operations.Type: GrantFiled: January 5, 1994Date of Patent: July 11, 1995Assignee: Nippon Shinyaku Company LimitedInventors: Shoichi Chokai, Shinji Ohmachi, Masafumi Taira
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Patent number: 5364880Abstract: Described is a novel compound and method, useful for treatment of cardiac arrhythmias, especially useful in patients with congestive heart failure (CHF). A process for synthesizing the novel compound is also described.Type: GrantFiled: June 16, 1993Date of Patent: November 15, 1994Assignee: Advanced Therapies, Inc.Inventor: Pascal Druzgala
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Patent number: 5360815Abstract: 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: June 23, 1993Date of Patent: November 1, 1994Assignee: Merck Frosst Canada, Inc.Inventors: Rejean Fortin, Yves Girard, Erich Grimm, John Hutchinson, John Scheigetz
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Patent number: 5274000Abstract: A new series of benzofuran and benzothiophene derivatives are disclosed. These compounds have a structure which can be obtained by substituting the third position of 2-lower alkyl-benzofuran or 2-lower alkyl-benzothiophene with a substituted benzene derivative, itaconic acid derivative or a substituted phenoxymethyl tetrazole derivative. They are useful as diuretics without side effects of elevating serum uric acid levels and can be used in the treatment of hyperuricemia.Type: GrantFiled: April 21, 1992Date of Patent: December 28, 1993Assignee: Kotobuki Seiyaku Company LimitedInventors: Tsuyoshi Tomiyama, Akira Tomiyama, Koichi Kubota
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Patent number: 5266711Abstract: The invention relates to a process for the preparation of 3-benzoyl benzofuran derivatives of general formula: ##STR1## wherein a benzofuran derivative of general formula: ##STR2## is reacted in situ in the presence of aluminium chloride successively with phosgene or oxalyl chloride, and then with a phenolic derivative of general formula: ##STR3## to produce a complex which is hydrolysed to form the desired compound of 3-benzoyl benzofuran.Type: GrantFiled: October 16, 1990Date of Patent: November 30, 1993Assignee: SanofiInventors: Bernard Boudet, Jean R. Dormoy, Alain Heymes
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Patent number: 5235068Abstract: Acylaromatic compounds ##STR1## (Q: aromatic compound residue; R: straight, branched or cyclic aliphatic group, aromatic group or araliphatic group) are prepared in high yield by a reaction, in the presence of a boron trifluoride complex catalyst, of an aromatic compound with ##STR2## (X: H, Cl, Br; Y: Cl, Br) or with RCOOH in the presence of (XYCHCO).sub.2 O.Type: GrantFiled: July 21, 1992Date of Patent: August 10, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Michitada Kondo, Yuji Ueda, Seiichi Kai, Takayuki Higashii
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Patent number: 5219886Abstract: Novel mercapto-acylamino acids of the formula ##STR1## wherein Q is hydrogen or R.sup.7 CO--;R.sup.1 is lower alkyl, cyclolower alkyl, aryl or heteroaryl;R.sup.2 is hydrogen; lower alkyl; cyclolower alkyl; lower alkyl substituted with hydroxy, lower alkoxy, mercapto, lower alkylthio, aryl or heteroaryl; aryl; or heteroaryl;R.sup.3 is --OR.sup.5 or --NR.sup.5 R.sup.6 ;R.sup.4 and R.sup.9 are independently --(CH.sub.2).sub.q R.sup.8, provided that when R.sup.4 and R.sup.9 are both hydrogen, R.sup.2 is biphenylyl, phenoxyphenyl, phenylthiophenyl, naphthyl, heteroaryl, or lower alkyl substituted with hydroxy, lower alkoxy, mercapto or lower alkylthio;R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl and aryl lower alkyl, or R.sup.5 and R.sup.6 together with the nitrogen to which they are attached form a 5-7 membered ring;R.sup.7 is hydrogen, lower alkyl or aryl;R.sup.Type: GrantFiled: October 1, 1991Date of Patent: June 15, 1993Assignee: Schering CorporationInventors: Elizabeth M. Smith, Philip M. DeCapite, Bernard R. Neustadt
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Patent number: 5194631Abstract: A process for producing a carboxylic acid which comprises reacting an organic chloride having at least one chloride atom on its ring of a substituted or unsubstituted, aromatic or heterocyclic hydrocarbon with carbon monoxide in the presence of an inorganic base or an organic base and water at a reaction temperature of 150.degree. to 300.degree. C., and preferably 160.degree. to 300.degree. C., by using as catalysts a palladium compound and a phosphine compound represented by the general formula (III):(R).sub.2 P--X--P(R).sub.2 (III)wherein R is an alkyl group or a substituted or unsubstituted phenyl group, and X is an alkylene group having 1 to 6 carbon atoms, ##STR1## or a binaphthyl group.Type: GrantFiled: July 11, 1989Date of Patent: March 16, 1993Assignee: Nihon Nohyaku Co., Ltd.Inventors: Keiji Suto, Koji Nakasa, Masaaki Kudo, Moriharu Yamamoto
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Patent number: 5182295Abstract: A compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl and alkynyl of up to 8 carbon atoms, optionally substituted cycloalkyl or cycloalkenyl of up to 8 carbon atoms, optionally substituted aryl of 6 to 18 carbon atoms, optionally substituted aralkyl of 7 to 24 carbon atoms, optionally substituted benzoyl and optionally substituted heterocycle, the optional substituents being at least one member of the group consisting of halogen, phenoxy, thiazolyl, alkyl and alkoxy of 1 to 6 carbon atoms and haloalkyl, Alk.sub.1 and Alk.sub.2 are individually optionally substituted alkyl of 1 to 8 carbon atoms, X is --O-- or --S-- and R' is hydrogen or halogen in any position on the phenyl and the geometry of the double bond is E or Z or a mixture of E and Z and having useful pesticidal properties.Type: GrantFiled: October 1, 1991Date of Patent: January 26, 1993Assignee: Roussel UclafInventors: Marc Benoit, Jean-Louis Brayer, Jean-Pierre Demoute, Gilles Mourioux, Laurent Taliani
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Patent number: 5122611Abstract: A method for producing an azomethine or indoaniline series dye, which comprises oxidatively condensing an active methylene- or methine-containing compound, except those containing a sulfonic or carboxylic acid group, and p-phenylenediamine, except those containing a sulfonic or carboxylic acid group, in the presence of methylene chloride as a solvent under a basic condition.Type: GrantFiled: August 23, 1990Date of Patent: June 16, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Mitsugu Tanaka, Hisashi Mikoshiba
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Patent number: 5118683Abstract: Compounds of the formula I ##STR1## wherein R.sup.5 represents C.sub.1 to C.sub.6 -alkyl or the group --(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --Ar;Z represents O, S or --CH.sub.2 --;n represents an integer of 1 to 8;m represents zero or an integer of 1 to 8;one of R.sup.1 and R.sup.2 represents the group ##STR2## and the other represents hydrogen or R.sup.7 CO--; R.sup.7 is C.sub.1 to C.sub.10 alkyl, C.sub.3 to C.sub.8 cycloalkyl, aryl, heteroaryl, --N(R.sup.9 R.sup.10), or R.sup.11 O--; R.sup.3, R.sup.4, R.sup.9, and R.sup.10 are each independently selected from hydrogen, C.sub.1 to C.sub.6 alkyl and Ar.sup.1 ; R.sup.6 and R.sup.11 are each independently C.sub.1 -C.sub.8 alkyl; Ar and Ar.sup.1 are each independently selected from the group consisting of phenyl or phenyl substituted by one or two substituents selected from the group consisting of R.sup.12, R.sup.13 O--; R.sup.14 S(O).sub.x --, R.sup.15 CO--, (R.sup.16 R.sup.17)NCO--, F, Cl, Br, I, NO.sub.2, CF.sub.3, CN, or phenyl; R.sup.12, R.sup.13, R.sup.Type: GrantFiled: June 13, 1990Date of Patent: June 2, 1992Assignee: Schering CorporationInventors: David J. Blythin, Ho-Jane Shue
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Patent number: 5089638Abstract: Analogs of glutamic acid and related amino acids and pharmaceutically-acceptable salts thereof which antagonize the function of cholecystokinins and gastrin disease states in animals and compositions for and methods of preventing or treating disorders of the gastrointestinal, central nervous and appetite regulatory systems of mammals, especially of humans.Type: GrantFiled: August 30, 1989Date of Patent: February 18, 1992Assignee: Merck & Co., Inc.Inventor: Roger M. Freidinger
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Patent number: 5081252Abstract: A process for the preparation of aromatic carboxylic acids or their salts comprises heating carboxyl-free aromatic compounds and aromatic carboxylic acid salts whose basic structures differ from those of the aromatic compounds, or heating polycyclic aromatic compounds with three or more rings and monocyclic or bicyclic aromatic carboxylic acid salts, under carbon dioxide pressure in the presence of one or more metal compounds selected from group (a) of compounds of zinc, cadmium, and thallium and one or more compounds selected from group (b) of compounds of cesium, Group II metals, And Group IIIa metals to effect the intermolecular transfer of the carboxyl groups.Type: GrantFiled: June 5, 1989Date of Patent: January 14, 1992Assignees: Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd.Inventors: Shuichi Mitamura, Yoshimi Kata, Koichi Fujishiro, Yasuhisa Tsutsumi
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Patent number: 5073552Abstract: Substituted benzophenones are disclosed having the following formula ##STR1## where R.sub.A and R.sub.B are each independently COOH, C.sub.1 to C.sub.12 linear or branched alkyl or taken together to form an anhydride ring, R is nitro or amino unsubstituted or substituted with at least one C.sub.1 to C.sub.6 linear or branched alkyl, phenyl or substituted phenyl, the substituents being one or more C.sub.1 to C.sub.6 linear or branched alkyl or C.sub.6 to C.sub.10 aryl, Y and Y' are the same or different and are a chemical bond ##STR2## and m is 0 or 1 with the proviso that both R.sub.A and R.sub.B can not be hydrogen.Processes to produce these benzophenones are also disclosed.Type: GrantFiled: September 4, 1990Date of Patent: December 17, 1991Assignee: Ethyl CorporationInventors: Mark W. Beltz, Venkataraman Ramachandran
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Patent number: 5059621Abstract: An aromatic heterocyclic compound has the formula ##STR1## wherein R.sub.1 represents (i) --CH.sub.3, (ii) --CH.sub.2 OH or (iii) ##STR2## wherein R.sub.3 represents hydrogen, --OR.sub.4 wherein R.sub.4 represents hydrogen, alkyl having 1-20 carbon atoms, mono- or polyhydroxyalkyl or R.sub.3 represents ##STR3## wherein r'and r" represent hydrogen or lower alkyl, R.sub.2 represents hydrogen or --CH.sub.3 and Ar represents ##STR4## wherein Z is O or S, ##STR5## wherein R.sub.5 is lower alkyl or ##STR6## wherein R.sub.6 is hydrogen or alkyl having 1-10 carbon atoms and R.sub.7 represents alkyl having 4-12 carbon atoms or cycloalkyl, Y is CH and X represents oxygen or sulfur, with the proviso that (i) when Y is CH and X is oxygen or sulfur Ar is other than C wherein R.sub.5 is CH.sub.3 and (ii) when Y is CH and X represents sulfur Ar is other than A.The compound is useful in the treatment of dermatologic ailments linked to a keratinization disorder.Type: GrantFiled: November 2, 1989Date of Patent: October 22, 1991Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 5039681Abstract: A novel piperidine derivative is defined by the formula (I), including a salt thereof, ##STR1## wherein R.sup.1 denotes a univalent group derived from one selected among substituted or unsubstituted benzene, pyridine, pyrazine, indole, anthraquinone, quinoline, substituted or unsubstituted phthalimide, homophthalimide, pyridinecarboxylic acid imide, pyridine N-oxide, pyrazinedicarboxylic acid imide, naphthalenedicarboxylic acid imide, substituted or unsubstituted quinazolinedione, 1,8-naphthalimide, bicyclo [2.2.2] oct-5-ene-2,3-dicarboxylic acid imide and pyromerylimide,X denotes a group of the formula --(CH.sub.2).sub.n --, a group of the formula --O(CH.sub.2).sub.n --, a group of the formula --S(CH.sub.2).sub.n --, a group of the formula --NH(CH.sub.2).sub.n --, a group of the formula --SO.sub.2 NH(CH.sub.2).sub.n --, a group of the formula ##STR2## a group of the formula ##STR3## a group of the formula ##STR4## a group of the formula --CH.sub.2 NH(CH.sub.2).sub.Type: GrantFiled: February 14, 1990Date of Patent: August 13, 1991Assignee: Eisai Co., Ltd.Inventors: Hachiro Sugimoto, Takaharu Nakamura, Yutaka Tsuchiya, Hiroyuki Sugumi, Kunizou Higurashi, Norio Karibe, Yoshiharu Yamanishi, Hiroo Ogura, Shin Araki, Atsuhiko Kubota, Michiko Ohtake, Kiyomi Tamatsu
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Patent number: 5017583Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are leukotriene antagonists. These compounds inhibit SRS-A and leukotriene synthesis and are antagonists of SRS-A and are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: February 23, 1988Date of Patent: May 21, 1991Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
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Patent number: 5017618Abstract: Compounds having the formula ##STR1## and their pharmaceutically acceptable acid addition salts, wherein --X-- is --O--, --CH.sub.2 -- or --; .dbd.Y is .dbd.O or a derivatized keto group which is hydrolyzable or enzymatically convertible to a keto group; R is alkyl having from 1 to 12 carbon atoms or aralkyl having from 7 to 20 carbon atoms; and Ar is the 3-aromatic or heterocyclic residue of a 1-alkylamino-2-propanol having an aromatic or heterocyclic substituent at the 3-position and having .beta.-adrenergic blocking properties; are useful as .beta.-adrenergic blocking agents and are of particular interest in the treatment of glaucoma or for lowering intraocular pressure.Type: GrantFiled: September 18, 1989Date of Patent: May 21, 1991Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 4990647Abstract: Unsymmetric biaryl compounds are prepared by coupling two different halogenoaromatics by reaction with a metal and carrying out the reaction in the presence of catalytic amounts of a nickel compound, a promoter and a phosphorus-containing ligand.Type: GrantFiled: April 24, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Thomas Himmler, Rudolf Braden
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Patent number: 4990668Abstract: Described is a process for preparing a racemic or chiral aryloxypropanolamine (1) or arylethanolamine (2) of the formula ##STR1## wherein Ar is aryl, substituted aryl, heteroaryl, or aralkyl and R is alkyl, substituted alkyl, aralkyl, or WB wherein W is a straight or branched chain alkylene of from 1 to about 6 carbon atoms and wherein B is --NR.sub.2 COR.sub.3, --NR.sub.2 CONR.sub.3 R.sub.4, --NR.sub.2 SO.sub.2 R.sub.3, --NR.sub.2 SO.sub.2 NR.sub.3 R.sub.4, or --NR.sub.2 COOR.sub.5, where R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.3 and R.sub.5 are not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.3 or --NR.sub.3 COOR.sub.5, or R.sub.3 and R.sub.4 may together with N form a 5- to 7-membered heterocyclic group.The process can be used to prepare beta-blocking agents, useful in the treatment of cardiac conditions.Type: GrantFiled: December 4, 1985Date of Patent: February 5, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Khuong H. X. Mai, Ghanshyam Patil, William L. Matier
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Patent number: 4988727Abstract: A compound selected from the group consisting of all enantiomeric and diastereoisomeric forms possible of compounds of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, halogen, and alkyl and alkoxy of 1 to 5 carbon atoms, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, one of A and B being ##STR2## and the other being ##STR3## R is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2).sub.n -- or branched alkylene of 2 to 8 carbon atoms, n is an integer from 0 to 5, Y is selected from the group consisting of naphthyl, indenyl, heterobicyclics and heteromonocyclic containing 5 to 6 ring members, all optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 5 carbon atoms, halogen, --OH, --CF.sub.3, --NO.sub.2, --NH.sub.Type: GrantFiled: September 19, 1989Date of Patent: January 29, 1991Assignee: Roussel UclafInventors: Francois Clemence, Michel Fortin
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Patent number: 4975458Abstract: New 2-alkyl-3-(4-hydroxy-3,5-di-tert-butylbenzoyl)benzofurans useful for treating cardiac arrhythmia, as well as pharmaceutical compositions containing these benzofurans and the method of treating cardiac arrhythmia therewith are disclosed.Type: GrantFiled: March 13, 1989Date of Patent: December 4, 1990Assignees: Taro Pharmaceuticals Industries, Ltd., Taro Vit Industries, Ltd.Inventors: Barrie Levitt, Morris Stolar, Ron Breiman
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Patent number: 4968821Abstract: 4,7-Benzofurandione derivatives of Formula I, pharmaceutical compositions, and methods of treatment are disclosed. These compounds are useful as inhibitors of mammalian leukotriene biosynthesis. As such, these compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular disorders, inflammation, psoriasis and allergic conjunctivitis. The compounds are also useful as analgesics and as cytoprotective agents. Also disclosed are novel intermediates useful for the preparation of the 4,7-benzofurandiones of this invention.Type: GrantFiled: July 11, 1988Date of Patent: November 6, 1990Assignee: Merck Frosst Canada, Inc.Inventors: Julian Adams, Yvan Guindon, Patrice C. Belanger, Michel L. Belley, Joshua Rokach
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Patent number: 4942169Abstract: A novel piperidine derivative is defined by the formula (I), including a salt thereof, ##STR1## wherein R.sup.1 denotes a univalent group derived from one selected among substituted or unsubstituted benzene, pyridine, pyrazine, indole, anthraquinone, quinoline, substituted or unsubstituted phthalimide, homophthalimide, pyridinecarboxylic acid imide, pyridine N-oxide, pyrazinedicarboxylic acid imide, naphthalenedicarboxylic acid imide, substituted or unsubstituted quinazolinedione, 1,8-naphthalimide, bicyclo [2.2.2.] oct-5-ene-2,3-dicarboxylic acid imide and pyromerylimide,X denotes a group of the formula --(CH.sub.2).sub.n --, a group of the formula --O(CH.sub.2).sub.n --, a group of the formula --S(CH.sub.2).sub.n --, a group of the formula --NH(CH.sub.2).sub.n --, a group of the formula --SO.sub.2 NH(CH.sub.2).sub.n --, a group of the formula ##STR2## a group of the formula ##STR3## a group of the formula ##STR4## a group of the formula --CH.sub.2 NH(CH.sub.2).sub.Type: GrantFiled: March 10, 1989Date of Patent: July 17, 1990Assignee: Eisai Co., Ltd.Inventors: Hachiro Sugimoto, Takaharu Nakamura, Yutaka Tsuchiya, Hiroyuki Sugumi, Kunizou Higurashi, Norio Karibe, Yoshiharu Yamanishi, Hiroo Ogura, Shin Araki, Atsuhiko Kubota, Michiko Ohtake, Kiyomi Tamatsu
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Patent number: 4918206Abstract: Highly effective diuretic antihypertensives, i.e., sulfamoyl-2-benzofurancarboxylic acid derivatives which are classified as loop diuretics with less adverse side-effects and can be administered orally at a daily dosage of 0.5 mg to 200 mg or parenterally at 0.01 mg to 50 mg.Type: GrantFiled: September 16, 1988Date of Patent: April 17, 1990Assignee: Shionogi & Co., Ltd.Inventors: Hiroshi Harada, Yoshihiro Matsushita, Masuhisa Nakamura, Yukio Yonetani
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Patent number: 4891383Abstract: New original derivatives are described of 5-pentylamino-5-oxopentanoic and 4-pentylamino-4-oxobutanoic acids having the formula: ##STR1## in which n is 1 or 2, R.sub.1 is selected from the groups 2-naphthyl, 2 (or 3)-quinolinyl, 2 (or 3)-indolyl, 2 (or 3)-benzofuranyl, 2 (or 3)-benzothiophenyl, and R.sub.2 is a pentyl group or an alkoxyalkyl group with 4 or 5 carbon atoms, preferably pentyl, 2-ethoxyethyl, 3-methoxypropyl or 3-ethoxypropyl.The compounds have a powerful antagonistic activity towards cholecystokinin and are particularly useful in the treatment of illnesses of the digestive system, such as colitis, biliary diskinesia, pancreatisis or in the treatment of disorders of the central nervous system imputable to deficiencies in the physiological neuron levels of cholecystokinin or other related bioactive polypeptides.Type: GrantFiled: December 7, 1988Date of Patent: January 2, 1990Assignee: Rotta Research Laborarorium S.p.A.Inventors: Francesco Makovec, Rolando Chiste, Walter Peris, Luigi Rovati
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Patent number: 4849431Abstract: A novel piperidine derivative or a pharmacologically acceptable salt thereof is used in the treatment and prevention of dementias and sequelae of cerebrovascular diseases. These compounds also exhibit strong, highly selective anticholinesterase activity and may be orally or parenterally administered.Type: GrantFiled: December 24, 1986Date of Patent: July 18, 1989Assignee: Eisai Co., Ltd.Inventors: Hachiro Sugimoto, Takaharu Nakamura, Yutaka Tsuchiya, Hiroyuki Sugumi, Kunizou Higurashi, Norio Karibe, Yoshiharu Yamanishi, Hiroo Ogura, Shin Araki, Atsuhiko Kubota, Michiko Ohtake, Kiyomi Tamatsu
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Patent number: 4831054Abstract: New 2-alkyl-3-[4-(omega-N,N-dialkylaminoacylamino)-3,5-dialkylbenzoyl]benzofur ans useful for treating cardiac arrhythmia, as well as pharmaceutical compositions containing these benzofurans and the method of treating cardiac arrhythmia therewith are disclosed.Type: GrantFiled: April 18, 1988Date of Patent: May 16, 1989Assignee: Taro Pharmaceuticals, Ltd.Inventors: Barrie Levitt, Morris Stolar, Ron Breiman
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Patent number: 4829067Abstract: Novel benzo-furan(or -thiophene) derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen atom, a lower alkyl group, a cycloalkyl group, a phenyl-lower alkyl group or a substituted or unsubstituted phenyl group, R.sup.2 is hydrogen atom, a lower alkyl group, an acyl group or phenyl group, R.sup.3 is hydrogen atom, a halogen atom, nitro group, a lower alkoxy group, amino group or an acylamino group, R.sup.4 is a group of the formula: ##STR2## A is a lower alkylene group optionally substituted with hydroxy group, B is single bond or a lower alkylene group, one of R.sup.5 and R.sup.6 is hydrogen atom or a lower alkyl group and the other is a lower alkyl group or a phenyl-lower alkyl group, or R.sup.5 and R.sup.6 combine together with adjacent nitrogen atom to form a heteromonocyclic group, R.sup.7 is a lower alkyl group, X is oxygen atom or sulfur atom, Y is oxygen atom, imino group, a lower alkylimino group or a phenyl-lower alkylimino group and a salt thereof are disclosed.Type: GrantFiled: December 2, 1987Date of Patent: May 9, 1989Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Ikuo Iijima, Masakatsu Ozeki, Yutaka Saiga, Tohru Ishizuka, Kunio Nosaka
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Patent number: 4826878Abstract: New original derivatives are described of 5-pentylamino-5-oxopentanoic and 4-pentylamino-4-oxobutasnoic acids having the formula: ##STR1## in which n is 1 or 2, R.sub.1 is selected from the groups 2-naphthyl, 2 (or 3)-quinolinyl, 2 (or 3)-indolyl, 2 (or 3)-benzofuranyl, 2 (or 3)-benzothiophenyl, and R.sub.2 is a pentyl group or an alkoxyalkyl group with 4 or 5 carbon atoms, preferably pentyl, 2-ethoxyethyl, 3-methoxypropyl or 3-ethoxypropyl.The compounds have a powerful antagonistic activity towards cholecystokinin and are particularly useful in the treatment of illnesses of the digestive system, such as colitis, biliary diskinesia, pancreatitis or in the treatment of disorders of the central nervous system imputable to deficiencies in the physiological neuron levels of cholecystokinin or other related bioactive polypeptides.Type: GrantFiled: December 16, 1987Date of Patent: May 2, 1989Assignee: Rotta Research Laboratorium S.p.A.Inventors: Francesco Makovec, Rolando Chiste, Walter Peris, Luigi Rovati
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Patent number: 4791209Abstract: Novel furobenzisoxazole derivatives of the formula (I): ##STR1## (wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different represent a hydrogen atom, a halogen atom, or a lower alkyl group having 1-4 carbon atoms; R.sub.5 is a hydroxymethyl group, a carboxyl group or a lower alkoxy carbonyl group having 1-3 carbon atoms; and X is a sulfur atom or a --CH.dbd.CH-- group), as well as intoxic salts thereof when R.sub.5 is a carboxyl group, and process for preparing the same are disclosed.The derivatives of formula (I) and nontoxic salts thereof have hypotensive, uricosuric and diuretic activities and hence ae useful as therapeutics for treating hyperuricemia, edema and hypertension.Type: GrantFiled: May 6, 1986Date of Patent: December 13, 1988Assignee: Chugai Seiyako Kabushiki KaishaInventors: Haruhiko Sato, Hiroshi Koga, Takashi Dan, Etsuro Onuma
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Patent number: 4780480Abstract: Novel aroyl-substituted benzofuran and benzothiophene acetic and proprionic acids are disclosed herein. These compounds are useful as analgesic, anti-inflammatory, and antipyretic agents.Type: GrantFiled: April 20, 1987Date of Patent: October 25, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: James P. Dunn
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Patent number: 4778805Abstract: 4,7-Benzofurandione derivatives of Formula I, pharmaceutical compositions, and methods of treatment are disclosed. These compounds are useful as inhibitors of mammalian leukotriene biosynthesis. As such, these compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular disorders, inflammation, psoriasis and allergic conjunctivitis. The compounds are also useful as analgesics and as cytoprotective agents. Also disclosed are novel intermediates useful for the preparation of the 4,7-benzofurandiones of this invention.Type: GrantFiled: June 18, 1987Date of Patent: October 18, 1988Assignee: Merck Frosst CanadaInventors: Julian Adams, Yvan Guindon, Patrice C. Belanger, Michel L. Belley, Joshua Rokach
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Patent number: 4766223Abstract: The invention relates to new molecular complexes of general formula: ##STR1## in which R represents a straight- or branched-chain alkyl radical having from 1 to 4 carbon atoms and R.sub.1 represents one of the radicals: ##STR2## These molecular complexes are especially useful for the preparation of 2-alkyl-3-(4-hydroxybenzoyl)benzofurans.Type: GrantFiled: June 19, 1986Date of Patent: August 23, 1988Assignee: SanofiInventors: Claude Grain, Fernand Jammot
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Patent number: 4745127Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit the mammalian 5-lipoxygenase enzyme, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: January 7, 1987Date of Patent: May 17, 1988Assignee: Merck Frosst Canada, Inc.Inventors: Joseph G. Atkinson, Yvan Guindon, Cheuk K. Lau
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Patent number: 4713393Abstract: Phenylalkyl-2,3-dihydrobenzofurans and analogs were prepared by (1) nucleophilic substitution involving an appropriately substituted 2,3-dihydrobenzofuranol (or 2,3-dihydrobenzopyranol) and a cinnamylhalide followed by reduction; or (2) by Wittig reaction involving a halomethyl derivative of 2,3-dihydrobenzofuran (or 2,3-dihydrobenzopyran and an aryl or a heteroaryl aldehyde followed by reduction. These compounds were found to be potent anti-inflammatory agents.Type: GrantFiled: April 25, 1985Date of Patent: December 15, 1987Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Kathryn L. Thompson, David A. Boulton
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Patent number: 4666931Abstract: A benzofuran derivative having the general formula (I): ##STR1## wherein R.sup.1 is hydrogen atom, a benzyl group, unsubstituted or substituted with a halogen atom or an alkyloxy group, or an alkyl group having 1 to 3 carbon atoms, R.sup.2 is hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R.sup.3 is acetyl group, ethyl group, carboxyl group or 4-methyl-2,5-dioxoimidazolidine-4-yl group, R.sup.4 is hydrogen atom, hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, carboxymethoxy group, nitro group, acetoamino group, a benzylozy group unsubstituted or substituted with a halogen atom, nitro group or an alkyloxy group or a group having the formula: --OR.sup.6, wherein R.sup.6 is an alkenyl group having 2 to 4 carbon atoms or an alkyl group having 2 to 3 carbon atoms having a halogen atom, cyano group or oxo group, R.sup.5 is hydrogen atom or methylenedioxy group together with R.sup.Type: GrantFiled: December 27, 1985Date of Patent: May 19, 1987Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Yoshitaka Ohishi, Michiko Nagahara, Norio Kajikawa, Motoyuki Yajima, Katsumi Nogimori, Shigeki Kurokawa
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Patent number: 4664693Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: A is selected from CH and N;B is selected from oxygen, sulfur, CH.sub.2 and the group N-Z wherein Z is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, benzyl and substituted benzyl;X, which may be the same or different, and X.sup.1, which be the same or different, are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.Type: GrantFiled: April 13, 1984Date of Patent: May 12, 1987Assignee: ICI Australia LimitedInventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson, Murray L. Whitelaw
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Patent number: 4663347Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit the mammalian 5-lipoxygenase enzyme, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: April 19, 1985Date of Patent: May 5, 1987Assignee: Merck Frosst Canada, Inc.Inventors: Joseph G. Atkinson, Yvan Guindon, Cheuk K. Lau
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Patent number: 4659709Abstract: Highly effective diuretic antihypertensives, i.e., 2,3-dihydrobenzofuran-5-sulfonamide derivatives which is classified to loop diuretics with less adverse side-effects and can be administered orally at a daily dosage of 0.5-200 mg or parenterally of 0.01-50 mg.Type: GrantFiled: August 12, 1985Date of Patent: April 21, 1987Assignee: Shionogi & Co.Inventors: Hiroshi Harada, Yoshihiro Matsushita, Masuhisa Nakamura, Yukio Yonetani
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Patent number: 4654365Abstract: The invention relates to novel substituted 2,3-dihydro-5-(3-oxo-2-cyclohexen-1-yl)-2-benzofurancarboxylic acids, their derivatives and their salts. The compounds are useful for the treatment and prevention of injury to the brain and of edema due to head trauma, stroke (particularly ischemic), arrested breathing, cardiac arrest, Reye's syndrome, cerebral thrombosis, cerebral embolism, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections and various brain concussions.Type: GrantFiled: September 26, 1985Date of Patent: March 31, 1987Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
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Patent number: 4634783Abstract: Amidine compounds of the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful anti-trypsin, anti-plasmin, anti-kallikrein and anti-thrombin agents. They are also useful as a powerful anti-complement agent.Type: GrantFiled: January 23, 1984Date of Patent: January 6, 1987Assignee: Torii & Co. Ltd.Inventors: Setsuro Fujii, Toyoo Nakayama, Shigeki Nunomura, Ryoji Matsui, Shin-ichi Watanabe, Kimio Sudo, Toshiyuki Okutome, Masateru Kurumi, Yojiro Sakurai, Takuo Aoyama