Chalcogen Bonded Directly To The Ring Carbon Para To The Ring Oxygen (e.g., Chromones, Etc.) Patents (Class 549/401)
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Patent number: 4999439Abstract: Described are alkyl-substituted tetra- or hexahydrobenzopyran derivatives defined according to one of the generic structures: ##STR1## wherein Z is a moiety in the alternative either ##STR2## wherein in the moiety having the structure: ##STR3## R' is methyl or ethyl and in the moiety having the structure: ##STR4## one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds; wherein R.sub.1 and R.sub.2 taken separately represent hydrogen or C.sub.1 -C.sub.3 lower alkyl (with the proviso that R.sub.1 and R.sub.2 are not both hydrogen) or R.sub.1 and R.sub.2 taken together complete a C.sub.5 or C.sub.Type: GrantFiled: March 22, 1990Date of Patent: March 12, 1991Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna, Charles E. J. Beck, Salvatore M. Brucato
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Patent number: 4992564Abstract: Disclosed is a practical and efficient process for preparing 6-substituted 4-chromanones from phenolic acrylate ester compounds derivable from para-substituted phenolic or thiophenolic compounds and beta-unsubstituted acrylic acid compounds which are esterifiable therewith. The process includes effecting rearrangement of a phenolic or thiophenolic acrylate ester in the presence of a rearrangement effective amount of hydrogen fluoride to the corresponding hydroxy--or mercapto (vinyl ketone) wherein the carbonyl carbon atom of the vinyl carboxy group is directly attached to the benzene ring ortho to the hydroxy or mercapto group. Thereafter, the vinyl ketone is cyclized to the corresponding 6-substituted 4-chromanone in the presence of a cyclization-effective amount of hydrogen fluoride. The 6-substituted 4-chromanones prepared by the process are useful as intermediates for preparing pharmaceutical agents.Type: GrantFiled: August 31, 1989Date of Patent: February 12, 1991Assignee: Mallinckrodt, Inc.Inventors: Jerry R. Patton, Narayanasamy Gurusamy
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Patent number: 4987130Abstract: Substituted amino derivatives represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 each stand for an acyclic hydrocarbon residue or an alicyclic hydrocarbon residue; R.sup.3 and R.sup.4 each stand for hydrogen or a hydrocarbon residue optionally containing hetero-atom(s); A stands for a carbon chain having two or more carbon atoms optionally containing ether linkage or sulfide linkage, which may be substituted and which may per se form a ring; X.sup.1 and X.sup.2 each stand for oxygen atom or sulfur atom; and Y stands for amino group or an organic residue bonded through nitrogen atom, which may form a ring by combining with a carbon atom constituting A; and their salts have anti-arrhythmic activity and are useful for prevention and treatment of a variety of arrhythmias.Type: GrantFiled: December 22, 1989Date of Patent: January 22, 1991Assignee: Takeda Chemical Industries, Ltd.Inventors: Susumu Tsushima, Muneo Takatani, Minoru Hirata
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Patent number: 4985429Abstract: Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives, such as l-N-[3-(2,3-dihydro-1-oxo-1H-inden-5-yl)-2-oxooxazolidin-5-ylmethyl]acetam ide, possess useful antibacterial activity.Type: GrantFiled: March 15, 1990Date of Patent: January 15, 1991Assignee: E. I. du Pont de Nemours and CompanyInventors: Chia-Lin J. Wang, Mark A. Wuonola
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Patent number: 4983603Abstract: The invention relates to novel tricyclic derivatives which are agonists of cholinergic receptors.These derivatives have the formula ##STR1## in which X=O, S, --OCH.sub.2 -- or --SCH.sub.2 --; R.sub.1 =H or halogen; and R.sub.2 = ##STR2## in which Alk is an alkylene group and R.sub.3, an R.sub.4, which are identical or different, are hydrogen or a lower alkyl group, or R.sub.3 and R.sub.4, with the nitrogen atom to which they are bonded, form a 5- or 6-membered cyclic amino group optionally containing a second heteroatom; or R.sub.2 is a group ##STR3## where R.sub.5 =C.sub.1 -C.sub.4 -alkyl. Application: agonists of cholinergic receptors.Type: GrantFiled: December 23, 1988Date of Patent: January 8, 1991Assignee: Societe Anonyme: SANOFIInventors: Camille G. Wermuth, Paul Worms, Jean-Jacques Bourguignon, Roger Brodin
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Patent number: 4968819Abstract: The invention relates to a process for the preparation of Chromenes of the general Formula V ##STR1## prepared from chromanone derivatives.Type: GrantFiled: September 7, 1989Date of Patent: November 6, 1990Assignee: Alkaloida Vegyeszeti GyarInventors: Tibor Timar, Kalman Zsupan, Janos Repasi, Iren Borsos nee Spafranek, Istvan Kiss, Andras Fodor, Peter Maroy
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Patent number: 4954518Abstract: This invention relates to a 4H-1-benzopyran-4-one derivative represented by the formula: ##STR1## or a salt thereof, a process for producing the same and a pharmaceutical composition comprising the same as active ingredient.Type: GrantFiled: October 7, 1988Date of Patent: September 4, 1990Assignee: Toyama Chemical Company, Ltd.Inventors: Shuntaro Takano, Chosaku Yoshida, Takihiro Inaba, Keiichi Tanaka, Ryuko Takeno, Hideyoshi Nagaki, Tomoya Shimotori, Shinji Makino
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Patent number: 4952705Abstract: The invention relates to compounds of the formula: ##STR1## which are useful as leukotriene D.sub.4 (LTD.sub.4) inhibitors and therefore useful in the treatment of allergies and inflammatory conditions.Type: GrantFiled: February 12, 1987Date of Patent: August 28, 1990Assignee: G. D. Searle & Co.Inventors: Masateru Miyano, Robert L. Shone, Daniel D. Sohn
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Patent number: 4950684Abstract: This invention relates to novel compounds having a 2,2-di-substituted chromanonyl (benzopyran) ring structure which are antagonists of leukotriene D.sub.4 (LTD.sub.4) and the slow reacting substance of anaphylaxis (SRS-A). The compounds of this invention are useful as pharmaceutical agents to prevent or alleviate the symptoms associated with LTD.sub.4, such as allergic reactions and inflammatory conditions.Type: GrantFiled: May 20, 1988Date of Patent: August 21, 1990Assignee: G. D. Searle & Co.Inventors: Francis J. Koszyk, James R. Deason
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Patent number: 4935529Abstract: Several new, biologically active substances have been isolated from Hormothamnion enteromorphoides, a somewhat rare cyanophyte from Puerto Rico.Hormothamnion, a lipophilic metabolite from this alga, has the styrylchromone structure: ##STR1## Hormothamnion and, to a lesser extent, one of its homologs, are potent cytotoxins to some types of cancer cells and appear to exert this cytotoxic action by a selective inhibition of RNA synthesis.A peptide compound of about 11 to 12 amino acids has antimicrobial activity, particularly against Candida albicans. The peptide, which includes phenylalanine, serine and other aliphatic amino acids, has blocked carboxyl and amino termini.Type: GrantFiled: March 6, 1989Date of Patent: June 19, 1990Assignee: State of Oregon acting by and through the Oregon State Board of Higher Education on behalf of Oregon State UniversityInventor: William H. Gerwick
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Patent number: 4918203Abstract: Disclosed is a practical and efficient process for preparing 6-substituted 4-chromanones from phenolic acrylate ester compounds derivable from para-substituted phenolic or thiophenolic compounds and beta-unsubstituted acrylic acid compounds which are esterifiable therewith. The process includes effecting rearrangement of a phenolic or thiophenolic acrylate ester in the presence of a rearrangement effective amount of hydrogen fluoride to the corresponding hydroxy - or mercapto (vinyl ketone) wherein the carbonyl carbon atom of the vinyl carboxy group is directly attached to the benzene ring ortho to the hydroxy or mercapto group. Thereafter, the vinyl ketone is cyclized to the corresponding 6-substituted 4-chromanone in the presence of a cyclization-effective amount of hydrogen fluoride. The 6-substituted 4-chromanones prepared by the process are useful as intermediates for preparing pharmaceutical agents.Type: GrantFiled: February 3, 1988Date of Patent: April 17, 1990Assignee: Mallinckrodt Inc.Inventors: Jerry R. Patton, Narayanasamy Gurusamy
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Patent number: 4904690Abstract: A novel chromone derivative having a strong antitumor activity of the general formula: ##STR1## wherein R.sup.1 is an unsaturated alkyl or cycloalkyl group having 3 to 7 carbon atoms; R.sup.2 is hydrogen atom or a halogen atom; R.sup.3 is hydrogen atom or a lower alkyl group; and X is carboxyl group, or its salt, ester or amide.Type: GrantFiled: March 1, 1988Date of Patent: February 27, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Tetsuya Aono, Katsutoshi Mizuno
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Patent number: 4889871Abstract: This invention encompasses compounds of Formula 1 and the pharmaceutically acceptable salts thereof. ##STR1## wherein R.sup.1 represents alkyl having 2-6 carbon atoms;R.sup.2 represents methyl or ethyl;R.sup.3 represents alkyl having 1 to 5 carbon atoms;W represents (CH.sub.2).sub.x where x is 2 to 7, alkylene having 2 to 7 carbon atoms, alkenylene having 3 to 7 carbon atoms, alkynylene having 3 to 7 carbon atoms, or cyclopentyl;R.sup.4 represents hydrogen, alkyl having 2-5 carbon atoms, alkenyl having 2 to 5 carbon atoms, or alkynyl having 2 to 5 carbon atoms;Q represents oxygen or CH.sub.2 ;B represents CH.sub.2, C.dbd.O or CH--OH;R.sup.5 represents hydrogen, alkyl having 1 to 6 carbon atoms, or R.sup.5 and R.sup.6 together optionally represent a carbon to carbon bond; orR.sup.5 represents alkanoyl having 2 to 4 carbon atoms, carboxy, alkoxycarbonyl, or (CH.sub.2)y--CO.sub.2 R.sup.8 wherein y is 0 to 4 and R.sup.8 is hydrogen or alkyl having 1 to 6 carbon atoms; andA represents --Z--CO.sub.2 R.sup.Type: GrantFiled: May 12, 1988Date of Patent: December 26, 1989Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Robert L. Shone, Stella S. T. Yu
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Patent number: 4841076Abstract: A benzopyran derivative represented by formula ##STR1## wherein: R.sub.1 and R.sub.2 each represents a hydrogen atom, a lower alkyl group, a substituted or unsubstituted cyclic alkyl group, a mono- or di-lower alkylamino group, a substituted or unsubsituted cyclic amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group;Y.sub.1 and Y.sub.2 each represents a hydrogen atom, a lower alkyl group, a halogen atom or a trihalomethyl group;Z represents a caroxyl group, a lower alkoxy-carbonyl group, a tetrazolyl group, a hydroxyl group or --CONR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 each represents a hydrogen atom or a lower alkyl group;n represents an integer of from 1 to 6; andthe bond between the 2- and 3-positions represents a single bond or a double bond;provided that a combination wherein Y.sub.1, Y.sub.2, and R.sub.2 each represents a hydrogen atom, R.sub.Type: GrantFiled: June 4, 1987Date of Patent: June 20, 1989Assignee: Daiichi Seiyaku Co., Ltd.Inventors: Masayuki Kitagawa, Makoto Tanaka
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Patent number: 4785004Abstract: Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: R.sup.0 represents hydrogen or C.sub.1-7 -alkanoyl,R.sup.1 represents C.sub.1-3 -alkyl which may be substituted by one or more halogen atoms having an atomic number of at most 17,R.sup.2 represents an aliphatic radical having from 5 to 15 carbon atoms,A represents ethylene, a single bond or vinylene,B.sup.1 represents C.sub.1-7 -alkylene or phenylene,B.sup.2 represents a single bond, ethylene or phenylene, andM represents an aromatic radical of the partial formula ##STR2## in which the symbols have the following meanings: R.sup.3 represents hydrogen or C.sub.1-4 -alkyl,X represents NH, O, S or if R.sup.4 represents hydrogen, a single bond,one of the symbols R.sup.4 and R.sup.5 represents hydrogen and the other represents the group --CO--R.sup.6, orR.sup.4 and R.sup.5 together represent the radical --CO--C(R.sup.6).dbd.C(R.sup.7)--or--CO--C(R.sup.7).dbd.C(R.sup.6)--orR.sup.4 R.sup.Type: GrantFiled: December 15, 1986Date of Patent: November 15, 1988Assignee: Ciba-Geigy CorporationInventors: Andreas Von Sprecher, Werner Breitenstein, Andreas Beck, Robert W. Lang, Konrad Oertle
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Patent number: 4780469Abstract: A (fused) benz(thio)amide of the formula: ##STR1## wherein B represents(i) a carbocyclic ring of from 4 to 8 members being unreplaced or replaced one, two or three of optional carbon atom(s) by oxygen, nitrogen and/or sulphur atom(s) or(ii) a divalent group of the formula: ##STR2## R.sup.1 represents a group of formula: ##STR3## (iv) a straight or branched alkyl, alkenyl, or alkynyl of from 1 to 20 carbon atoms,R.sup.4 represents(i) when B represents a closed ring, a group of the formula: ##STR4## (ii) when B does not represent a ring, a group of formula: ##STR5## with the proviso that compounds of formula: ##STR6## wherein A' is a vinylene or an ethylene group optionally substituted by straight or branched alkyl groups of from 1 to 4 carbon atom(s);R.sup.4' is--(CH.sub.2).sub.n --COOR.sup.8andR.sup.1' is(i) a group of the formula: ##STR7## or (ii) a group of the formula: ##STR8## are excluded, wherein A, R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8, U, n, m, p, q, R.sup.5', and R.sup.Type: GrantFiled: August 20, 1985Date of Patent: October 25, 1988Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Tumoru Miyamoto, Yoshinobu Arai
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Patent number: 4761425Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory agents, and cytoprotective agents.Type: GrantFiled: December 24, 1984Date of Patent: August 2, 1988Assignee: Merck Frosst Canada, Inc.Inventors: Yves Girard, Joshua Rokach
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Patent number: 4742077Abstract: Compounds of formula I ##STR1## wherein R.sub.1 represents a group of formula ##STR2## whereby R.sub.4 and R.sub.5 are the same or different and represent hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl and X represents oxygen, sulfur, imino, lower alkylimino, --(CH.sub.2)--, --(S.CH.sub.2)-- or --(O.CH.sub.2)--,R.sub.2 represents hydrogen or lower alkyl,R.sub.3 represents a group of formula ##STR3## whereby R.sub.6, R.sub.7 and R.sub.8 are the same or different and represent hydrogen or alkyl or R.sub.6 together with R.sub.7 or R.sub.7 together with R.sub.8 represent --(CH.sub.2).sub.m -- wherein m is 3 to 6,R.sub.9 represents alkyl, alkenyl, trialkylsilyl or alkyl substituted by hydroxy, lower alkoxy, lower halogenalkyl or aryl andn stands for 1, 2 or 3,which possess pharmaceutical in particular antimycotic activity as well as activity against phytopathogenic fungi.Type: GrantFiled: September 8, 1986Date of Patent: May 3, 1988Assignee: Sandoz Ltd.Inventor: Anton Stutz
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Patent number: 4680404Abstract: Bicyclic fused benzenoid compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, where M is O, CH.sub.2 or NR.sub.6 ; R.sub.6 is hydrogen, formyl, carbobenzyloxy or certain carboalkoxyalkyl, alkanoyl, alkyl, aralkyl or aralkylcarbonyl groups;A' is:(1) A where one of A and B is hydrogen such that when A is hydrogen, B is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 1 or 2; when B is hydrogen, A is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 0 or 1, when taken together A and OR.sub.1 form a lactone or certain derivatives thereof;(2) A' is ##STR2## (3) A' is Q.sub.3 ; Q is CO.sub.2 R.sub.7, COR.sub.8, C(OH)R.sub.8 R.sub.9, CN, CONR.sub.12 R.sub.13, CH.sub.2 NR.sub.12 R.sub.13, CH.sub.2 NHCOR.sub.14, CH.sub.2 NHSO.sub.2 R.sub.17 or 5-tetrazoyl;Q.sub.3 is ##STR3## 5-tetrazolyl, CH.sub.2 CONHCOR.sub.7, COOH or certain ester, amide, carboximido or sulfonimido derivatives thereof, CONHOH, CONHCONH.sub.2, or COCH.sub.2 Q.sub.4 and Q.sub.Type: GrantFiled: August 9, 1984Date of Patent: July 14, 1987Assignee: Pfizer Inc.Inventors: James F. Eggler, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4665203Abstract: The invention relates to compounds of the formula: ##STR1## which are useful as leukotriene D.sub.4 (LTD.sub.4) inhibitors and therefore useful in the treatment of allergies and inflammatory conditions.Type: GrantFiled: August 12, 1985Date of Patent: May 12, 1987Assignee: G. D. Searle & Co.Inventors: Masateru Miyano, Robert L. Shone, Daniel D. Sohn
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Patent number: 4665097Abstract: Novel bicyclooxyaryl thioureas are provided together with methods for their preparation and use as the active toxicant in pesticidal compositions.Type: GrantFiled: March 31, 1983Date of Patent: May 12, 1987Assignee: Union Carbide CorporationInventor: Paul A. Cain
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Patent number: 4650812Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkyl, R.sup.2 is hydrogen or halogen, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is hydrogen or lower alkyl, R.sup.5 is hydrogen, lower alkyl or aralkyl, X is alkylene and n is an integer from 1 to 6,enantiomers thereof, and, when R.sup.5 is hydrogen, salts thereof with pharmaceutically acceptable bases.Type: GrantFiled: January 18, 1985Date of Patent: March 17, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Noal Cohen, Guiseppe F. Weber
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Patent number: 4647579Abstract: Novel substituted 4-hydroxy-benzopyrans of the formula ##STR1## in which X is a single bond, ##STR2## and the other radicals can have various meanings, or pharmaceutically acceptable addition salts thereof, which are active on the circulation system.Type: GrantFiled: March 21, 1985Date of Patent: March 3, 1987Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Kabbe, Arno Widdig, Ulrich Niewohner, Andreas Knorr, Bernward Garthoff, Stanislav Kazda
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Patent number: 4628107Abstract: Novel chromone-8-aldehydes and thiochromone-8-aldehydes, useful in making pharmaceutically active dihydropyridines, of the formula ##STR1## in which R.sub.1 represents hydrogen, a C.sub.1 -C.sub.10 aliphatic hydrocarbon radical, a C.sub.1 -C.sub.10 alkyl carboxylate, or an aromatic or heteroaromatic ring which optionally has 1-5 identical or different halogen, C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy, C.sub.1 -C.sub.10 -alkylthio, C.sub.1 -C.sub.10 -alkylsulphinyl, cyano, hydroxyl, nitro, C.sub.1 -C.sub.5 -monofluoroalkyl or polyfluoroalkyl, C.sub.1 -C.sub.5 monofluoroalkoxy or polyfluoroalkoxy, C.sub.1 -C.sub.6 monofluoroalkylthio or polyfluoroalkylthio, amino, C.sub.1 -C.sub.5 -monoalkylamino or C.sub.1 -C.sub.5 dialkylamino substituents,R.sub.2 represents hydrogen or 1 to 3 halogen atoms, A represents a single bond, a C.sub.1 -C.sub.20 alkylene chain or a C.sub.2 -C.sub.Type: GrantFiled: June 28, 1985Date of Patent: December 9, 1986Assignee: Bayer AktiengesellschaftInventors: Siegfried Goldmann, Gerhard Franckowiak, Matthias Schramm, Gunter Thomas, Rainer Gross
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Patent number: 4625042Abstract: The present invention relates to 3-(4-fluorophenoxy)propionitrile having the formula (I): ##STR1## a process for preparing 3-(4-fluorophenoxy)propionitrile having the formula (I) which comprises reacting 4-fluorophenol and acrylonitrile in the presence of a tertiary amine, a process for preparing 6-fluoro-4-chromanone having the formula (II): ##STR2## which comprises reacting 3-(4-fluorophenoxy)propionitrile having the formula (I) with an acid, and a process for preparing 6-fluoro-4-chromanone having the formula (II) which comprises reacting 4-fluorophenol with acrylonitrile in the presence of a catalyst to give 3-(4-fluorophenoxy)propionitrile having the formula (I), which is then reacted with an acid. 6-Fluoro-4-chromanone is an important intermediate for the synthesis of (S)-2,3-dihydro-6-fluoro-spiro[4H-1-benzopyran-4,4'-imidazolidine]-2',5'di one (USAN: sorbinil).Type: GrantFiled: July 8, 1985Date of Patent: November 25, 1986Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Satomi Takahashi, Yasuyoshi Ueda, Yoshio Shimada, Kiyoshi Watanabe
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Patent number: 4609744Abstract: 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: March 19, 1984Date of Patent: September 2, 1986Assignee: Merck Frosst Canada Inc.Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
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Patent number: 4602034Abstract: The invention concerns: (oxo-4-4H-(1)-benzopyran-8-yl) alkanoic acids and their derivatives, their manufacture, represented by the formula: ##STR1## where Ar is hydrogen, a phenyl radical which may or may not be substituted, thenyl, furyl, naphthyl, a lower alkyl, cycloalkyl, aralkyl radical; B is a linear or branched lower alkyl radical, either saturated or ethylinically unsaturated; R.sub.1 is hydrogen or a phenyl radical; X is hydrogen or a lower alkyl or alkoxy radical and n=1, as well as salts, esters, aminoesters and amides.Compounds and their derivatives may be used as medicines, in particular in the control of tumors.Type: GrantFiled: November 6, 1984Date of Patent: July 22, 1986Assignee: Lipha, Lyonnaise Industrielle PharmaceutiqueInventors: Philippe Briet, Jean-Jacques Berthelon, Francois Collonges
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2,4-diamino-(substituted-benzopyran(quinolyl,isoquinoly)methyl)pyrimidine s useful as antibacterials
Patent number: 4587342Abstract: Novel 2,4-diaminopyrimidines having substituted heterobicyclomethyl moieties in the 5-position have superior antibacterial properties.Type: GrantFiled: October 31, 1983Date of Patent: May 6, 1986Inventors: Susan M. Daluge, Paul M. Skonezny -
Patent number: 4571405Abstract: Certain 5-substituted chromones and thiochromones and pharmacologically acceptable salts thereof are disclosed. The compounds possess antiallergic properties and are represented by the formula: ##STR1## wherein: X is selected from the group consisting of --O--, --S--, and --SO.sub.2 --;R.sub.1 and R.sub.2 are each independently H or lower alkyl having from 1 to 4 carbon atoms or together with C.sub.2 and C.sub.3 from a cyclohexane ring having the structure: ##STR2## wherein R.sub.3 and R.sub.4 are each independently H or a lower alkyl having from 1 to 4 carbon atoms.Also taught are valuable intermediates useful in the preparation of said 5-substituted chromones and thiochromones represented by the formula: ##STR3## wherein B is selected from the group consisting of --NHCOC(CH.sub.3).sub.3, 1,3-oxazolinyl and --CONHR, wherein R is methyl, phenyl, or t-butyl; Y is selected from the group consisting of CO.sub.2 H, CHO, CO.sub.Type: GrantFiled: May 29, 1984Date of Patent: February 18, 1986Assignee: Miles Laboratories, Inc.Inventors: Trevor S. Abram, Peter Norman, Warren, Brian T.
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Patent number: 4565882Abstract: The invention relates to substituted dihydrobenzopyrans carboxylates of the formula: ##STR1## wherein A is a methylene chain having 1-10 carbon atoms, inclusive, optionally substituted by hydroxy;wherein V is:(a) hydrogen;(b) hydroxy;(c) .dbd.O; or(d) R.sub.6 CH.sub.2 O--;wherein R.sub.1 is:(a) --COCH.sub.3 ;(b) --CHOHCH.sub.3 ;(c) --C.sub.2 H.sub.5 ;(d) -hydrogen; or(e) --COOC.sub.2 H.sub.5wherein R.sub.2 is:(a) -hydrogen;(b) -hydroxy; or(c) R.sub.12 CH.sub.2 CO.sub.2 --;wherein R.sub.3, R.sub.4, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 each of which may be the same or different, are:(a) hydrogen;(b) lower-alkyl having 1-6 carbon atoms inclusive; or(c) allyl;wherein R.sub.5 is:(a) hydrogen; or(b) R.sub.7 CH.sub.2 C(O)--;wherein R.sub.13 is hydrogen, hydroxy, alkoxy of 1 to 6 carbon atoms inclusive, or --OM wherein M is an alkali metal, alkyl of 1 to 6 carbon atoms, inclusive, or NR.sub.8.sup..sym. R.sub.9 R.sub.10 R.sub.11, or HNR.sub.8.sup..sym. R.sub.9 R.sub.Type: GrantFiled: January 6, 1984Date of Patent: January 21, 1986Assignee: G. D. Searle & Co.Inventors: Masateru Miyano, Robert L. Shone
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Patent number: 4551542Abstract: 6-Fluoro-4-chromanone can be regenerated from (R)-6-fluoro-4-ureidochroman-4-carboxylic acid, or from mixtures of (R)-6-fluoro-4-ureidochroman-4-carboxylic acid and its racemic modification, by oxidation with a permanganate, especially potassium permanganate. 6-Fluoro-4-chromanone is a chemical intermediate useful for preparing sorbinil, an aldose reductase inhibitor which can be used in clinical medicine for the control of the chronic complications of diabetes. (R)-6-Fluoro-4-ureidochroman-4-carboxylic acid and its racemic modification are by-products from the production of sorbinil from 6-fluoro-4-chromanone.Type: GrantFiled: September 26, 1984Date of Patent: November 5, 1985Assignee: Pfizer Inc.Inventor: Bernard S. Moore
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Patent number: 4546194Abstract: This invention relates to substituted chromanon-2-yl alkanols and derivatives thereof, which are useful as leukotriene D.sub.4 (LTD.sub.4) inhibitors and therefore useful in the treatment of allergies, inflammatory conditions, and coronary vasoconstriction.Type: GrantFiled: May 29, 1984Date of Patent: October 8, 1985Assignee: G. D. Searle & Co.Inventors: Masateru Miyano, Clara I. Villamil, Robert L. Shone
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Patent number: 4515975Abstract: Chroman derivatives of the general formula I ##STR1## where A--B is --CH.sub.2 --CH.sub.2 --(Ia), --CH.dbd.CH--(Ib), --CHOH--CH.sub.2 --(Ic) or --CO--CH.sub.2 --(Id), R.sup.1 is --CH.sub.2 --O--R' or ##STR2## where R' is C.sub.1 -C.sub.4 -alkyl or arylmethyl and R" and R'" are each C.sub.1 -C.sub.4 -alkyl, which can also be bonded to form a five-membered or six-membered cyclic acetal, R.sup.2 is C.sub.1 -C.sub.4 -alkyl and R.sup.3 is H or a protective group.Type: GrantFiled: November 4, 1982Date of Patent: May 7, 1985Assignee: BASF AktiengesellschaftInventors: Friedrich Vogel, Joachim Paust
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Patent number: 4495198Abstract: Chromone derivatives such as 6 or 7-(3-amino-2-hydroxypropoxy)-2-phenylchromones, -3-phenylchromones or -2,3-diphenylchromones which are useful as antihypertensive agents.Type: GrantFiled: November 15, 1982Date of Patent: January 22, 1985Assignee: Pennwalt CorporationInventor: Edwin S. Wu
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Patent number: 4479007Abstract: Chroman-4-ones are prepared by reacting an o-hydroxyarylcarbonyl compound with a carbonyl compound in the presence of an amine.Type: GrantFiled: July 23, 1979Date of Patent: October 23, 1984Assignee: Bayer AktiengesellschaftInventor: Hans-Joachim Kabbe
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Patent number: 4465851Abstract: A compound having the formula ##STR1## wherein R.sub.1 represents an indanyl, indolyl, quinolyl or chromonyl group, the group of the formula ##STR2## (in which R.sub.2 represents a halogen atom or a nitro group), or the group of the formula ##STR3## (in which R.sub.3 represents a halogen atom, or an alkyl, nitro, cyano, acetamino, aminosulfonyl, benzoyl, phenoxy or trifluoromethyl group, R.sub.4 represents a hydrogen or halogen atom, or an alkyl group, and R.sub.5 represents a hydrogen or halogen atom, or an alkyl group), or a pharmaceutically acceptable salt thereof. The compound is obtained by reacting 4-guanidinomethylcyclohexanecarboxylic acid or a reactive derivative thereof with a compound of the formula R.sub.1 --OH wherein R.sub.1 is the same as defined above, or a reactive derivative thereof.Type: GrantFiled: January 4, 1982Date of Patent: August 14, 1984Assignee: Nippon Chemiphar Co., Ltd.Inventors: Mutsumi Muramatsu, Toshio Satoh, Hiroyasu Sekine, Atsushi Tendo
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Patent number: 4464385Abstract: 6-Methythio and 6-methylsulfinyl spiro-chroman-imidazolidine diones useful in the treatment of complications arising from diabetes mellitus.Type: GrantFiled: April 15, 1982Date of Patent: August 7, 1984Assignee: Alcon Laboratories, Inc.Inventor: Billie M. York, Jr.
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Patent number: 4431828Abstract: 6-Fluoro-4-chromanone, a sorbinil intermediate, is regenerated from enantiomeric and mixtures of enantiomeric and racemic compounds obtained as major by-products in the synthesis of sorbinil. The regenerated intermediate is useful in the synthesis of additional sorbinil.Type: GrantFiled: November 10, 1982Date of Patent: February 14, 1984Assignee: Pfizer Inc.Inventors: Berkeley W. Cue, Jr., Philip D. Hammen, Stephen S. Massett
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Patent number: 4415741Abstract: Chroman-4-ones are prepared by reacting an o-hydroxyarylcarbonyl compound with a carbonyl compound in the presence of an amine.Type: GrantFiled: January 7, 1982Date of Patent: November 15, 1983Assignee: Bayer AktiengesellschaftInventor: Hans-Joachim Kabbe
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Patent number: 4394382Abstract: A benzopyran compound represented by the following ##STR1## wherein A represents a direct bond or the bond --CH.sub.2 --O--,R.sub.1 represents a member selected from the group consisting of a C.sub.3 -C.sub.5 alkyl group, a hydroxy-(C.sub.3 -C.sub.5 alkyl) group, a lower alkylamino-lower alkyl group, a nitrato-(C.sub.3 -C.sub.5 alkyl) group and a phenyl-(C.sub.1 -C.sub.5) alkyl group, provided that the phenyl may be substituted by a lower alkoxy group, R.sub.2 represents a member selected from the group consisting of hydrogen, halogen, OH, NO.sub.2, a carbamoyl group, a lower alkyl group, a lower alkoxy group, a lower alkyleneoxy group and acetyl group,R.sub.3 represents hydrogen or NO.sub.2,B represents a direct bond, a C.sub.1 -C.sub.7 alkylene group, a --O-lower alkylene group or a --CONH-lower alkylene group, andn represents 1 or 2;and an acid addition salt thereof and a pharmaceutical composition comprising aforesaid compound.Type: GrantFiled: June 9, 1981Date of Patent: July 19, 1983Assignee: Kowa Company, Ltd.Inventors: Masami Shiratsuchi, Noboru Shimizu, Hiromichi Shigyo, Yoshinori Kyotani, Hisashi Kunieda, Kiyoshi Kawamura, Seiichi Sato, Toshihiro Akashi, Masahiko Nagakura, Naotoshi Sawada, Yasumi Uchida
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Patent number: 4391821Abstract: The present invention relates to novel 7-substituted benzopyranes of formula (I), whereinR.sub.1 and R.sub.2 are hydrogen, alkyl of from 1 to 6 carbon atoms, hydroxyalkyl, alkenyl, cycloalkyl, phenylalkyl, dimethoxy-phenylalkyl, or R.sub.1 and R.sub.2 together with the joining nitrogen atom may represent a 5-7-membered heterocyclic ring,R.sub.3 is hydrogen, alkyl of from 1 to 4 carbon atoms or phenyl,R.sub.4 is hydrogen,R.sub.5 is hydrogen or phenyl, orR.sub.4 and R.sub.5 together may represent a bonding electron pair between the second and the third carbon atoms of the benzopyrane ring,R.sub.6 and R.sub.7 are hydrogen or they may represent an oxygen atom together,n is 1 or 2,with the proviso, that the pyrane ring may bear only one alkyl or phenyl substituent, and preparation process thereof.The novel compounds have valuable therapeutical effects, mainly in cardiotherapy.Type: GrantFiled: July 17, 1981Date of Patent: July 5, 1983Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.Inventors: Dezso Korbonits, Mihaly Nogradi, Borbala Vermes nee Szluha, Janos Strelisky, Andras Wolfner, Gergely Heja, Gabor Kovacz, Jozsef Szegi, Sandor Virag
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Patent number: 4376123Abstract: Basic ethers of the formula ##STR1## wherein Z is CH.sub.3 --NR.sup.2 --CH.sub.2 CH.sub.2 --CHR.sup.1 --, (1-R.sup.2 -3-piperidyl)-CHR.sup.3 --, (1-R.sup.2 -2-piperidyl)-CH.sub.2 --CHR.sup.3 - or 1-R.sup.2 -3-R.sup.4 -hexahydroazepinyl; R.sup.1 is cyclopropyl or Ar; R.sup.2 is H, alkyl of 1-4 C atoms, alkenyl of 2-4 C atoms, cycloalkylalkyl of 4-8 C atoms or benzyl; R.sup.3 is H or Ar; R.sup.4 is H or alkyl of 1-4 C atoms, Y is --O--CHQ.sup.1 --CHQ.sup.2 --CH.sub.2 --, --O--CHQ.sup.1 --CHQ.sup.2 --CO--, --O--CQ.sup.1 .dbd.CQ.sup.2 --CO-- or --CH.sub.2 --CHQ.sup.1 --CHQ.sup.2 --CO--; Q.sup.1 and Q.sup.2 are independently each H, alkyl of 1-4 C atoms, cycloalkyl or alkylcycloalkyl each of 3-6 total C atoms or Ar; and Ar is phenyl or phenyl substituted by F, Cl, alkoxy or alkylthio, each of 1-4 C atoms, methylenedioxy or CF.sub.3 ; with the proviso that when Z is (CH.sub.3 ).sub.2 N--CH.sub.2 CH.sub.2 --CHR.sup.1 in 7-position and Y is --O--C(C.sub.6 H.sub.5).dbd.CH--CO-- or --O--C(C.sub.6 H.sub.5).dbd.C(CH.sub.Type: GrantFiled: December 15, 1980Date of Patent: March 8, 1983Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Hans-Heinrich Hausberg, Helmut Prucher, Jurgen Uhl, Christoph Seyfried, Klaus Minck
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Patent number: 4371541Abstract: 3,4-Dihydro(or 1,4-dihydro)-4-aryl-2-[(substituted)thio]-[1]benzopyrano[3,4-d]imidazoles and their corresponding sulfoxides and sulfones, such as 3,4-dihydro(or 1,4-dihydro)-4-phenyl-2-[(1,1,2,2-tetrafluoroethyl)sulfonyl]-[1]benzopyran o[3,4-d]imidazole, are useful in the treatment of inflammation and/or pain.Type: GrantFiled: January 7, 1982Date of Patent: February 1, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: Michael Finizio
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Patent number: 4353906Abstract: Compounds of the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2 are independently selected from a hydrogen atom and a C.sub.1-3 alkyl group;R.sub.3 is a hydrogen atom, a C.sub.1-3 alkyl or C.sub.2-4 acyl group;R.sub.4 is a hydrogen atom or C.sub.1-5 alkyl group;R.sub.5 is a C.sub.1-5 alkyl group, a straight chain C.sub.1-3 alkyl group terminally substituted by a chlorine atom; orR.sub.4 and R.sub.5 are joined so that together with the nitrogen atom to which they are attached they form a 5-, 6- or 7-membered ring optionally containing an oxygen or sulphur atom;R.sub.6 is a C.sub.1-5 alkyl group;the NR.sub.4 R.sub.5 and OR.sub.3 moieties are trans; and pharmaceutically acceptable salts thereof having antihypertensive activity, processes for their preparation and their use in compositions.Type: GrantFiled: February 2, 1981Date of Patent: October 12, 1982Assignee: Beecham Group LimitedInventor: Graham A. Showell