Additional Chalcogen Bonded Directly To The Bicyclo Ring System Patents (Class 549/310)
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Patent number: 5256689Abstract: Disclosed herein are compounds of structural formula (I) ##STR1## which are useful as cholesterol lowering agents and as inhibitors of squalene synthase.Type: GrantFiled: October 26, 1992Date of Patent: October 26, 1993Assignee: Merck & Co., Inc.Inventor: Yuan-Ching P. Chiang
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Patent number: 5183907Abstract: Diphenyl ether derivatives of formula II ##STR1## wherein R.sub.1 represents a hydrogen or halogen atom or an alkyl or haloalkyl group, R.sub.2 and R.sub.3, which may be the same or different, each independently represents a hydrogen or halogen atom, or an alkyl, haloalkyl, nitro or cyano group, and R.sub.6 represents a hydrogen atom or an alkyl group, useful as intermediates in the preparation of diphenyl ether herbicides, are prepared by treating a compound of formula III ##STR2## where R.sub.1, R.sub.2 and R.sub.3 are as defined above with a dicarboxylic acid of formula R.sub.6 --CH(COOH).sub.2, where R.sub.6 is as defined above, in the presence of an organic base.Type: GrantFiled: October 29, 1991Date of Patent: February 2, 1993Assignee: Shell Internationale Research Maatschappij B.V.Inventor: Stuart P. Briggs
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Patent number: 5175312Abstract: Novel compounds of the formula I ##STR1## in which R.sub.1 is C.sub.13 -C.sub.30 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.7 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl, or is phenyl or C.sub.7 -C.sub.12 phenylalkyl, R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl and Z is phenyl, phenyl which is substituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.4 alkoxy or chlorine, a group ##STR2## in which n is 1 or 2 or a group ##STR3## in which the radicals A independently of one another are C.sub.1 -C.sub.8 alkyl, methoxy or ethoxy, are suitable for stabilizing organic material against oxidative, thermal and actinic degradation.Type: GrantFiled: August 27, 1991Date of Patent: December 29, 1992Assignee: Ciba-Geigy CorporationInventors: Paul Dubs, Rita Pitteloud
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Patent number: 5162550Abstract: Bisphthalide lactones of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxy, cyano, tetrahydrofuryl or lower alkoxy; or are acyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 10 carbon atoms or unsubstituted aralkyl or aryl, or aralkyl or aryl each substituted by halogen, cyano, nitro, trifluormethyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, --NX'X"-- or 4--NX'X--"phenylamino, wherein X' and X" are each independently of the other hydrogen, lower alkyl, cyclohexyl, benzyl or phenyl, or the pairs of substituents --NR.sub.1 R.sub.2 and --NR.sub.3 R.sub.4 are each a 5- or 6-membered, preferably saturated, heterocyclic radical, V.sub.1 and V.sub.2 are hydrogen, halogen, lower alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.Type: GrantFiled: August 24, 1990Date of Patent: November 10, 1992Assignee: Ciba-Geigy CorporationInventors: Rudolf Zink, Ian J. Fletcher
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Patent number: 5100456Abstract: The invention relates to the isolation, characterization and application of a bioherbicide composition characterized by its phytotoxcity towards the agricultural pest Convolvulus arvensis (field bindweed) and the aquatic weed Lemna paucicostata. The composition consists of a compound of formula I: ##STR1## wherein R.sub.1 is selected from H and OH, and R.sub.2 is selected from --CH.sub.2 OH and --COOH, salts and esters thereof, in association with an agriculturally acceptable carrier. The herbicide of this invention can be used for the control of field binweed and potentially other pest plants.Type: GrantFiled: July 12, 1990Date of Patent: March 31, 1992Assignee: Royal Institution for the Advancement of Learning (McGill University)Inventors: Youla S. Tsantrizos, Kelvin K. Ogilvie, Alan K. Watson
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Patent number: 5097044Abstract: Pyran-containing phthalides of the formula ##STR1## in which R is hydrogen, alkyl which has not more than 12 carbon atoms and is unsubstituted or substituted by halogen, cyano, hydroxyl or lower alkoxy, or is cycloalkyl, phenalkyl or phenyl each of which is unsubstituted or substituted, or an unsubstituted or substituted heterocyclic radical, R' is hydrogen, or R together with R' is C.sub.2 -C.sub.3 alkylene which is unsubstituted or substituted by methyl,X is hydrogen, alkyl having 1 to 12 carbon atoms or a monocyclic or polycyclic aromatic or heteroaromatic radical and the ring A is a benzene or naphthalene ring which is unsubstituted or monosubstituted or polysubstituted by halogen, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and the ring B is an aromatic or heteroaromatic radical which has 6 ring atoms and which can contain an aromatic fused ring, it being possible for both the ring B and the fused ring to be substituted.Type: GrantFiled: September 20, 1990Date of Patent: March 17, 1992Assignee: Ciba-Geigy CorporationInventor: Rox Phaff
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Patent number: 5077416Abstract: A heterocyclic compound of the formula, ##STR1## wherein A and B are each hydrogen, alkyl or alkoxy, Y is hydrogen, alkyl, alkoxy or --O--R.sup.2 --X--R.sup.1, or Y and B are taken together with each other to form methylenedioxy, R.sup.1 is alkyl, phenyl or alkenyl, R.sup.2 is unsubstituted or substituted alkylene, and X is --O--, --S--, --SO--, --SO.sub.2 -- or ##STR2## in which R.sup.3 is hydrogen or alkyl, with the proviso that R.sup.1 is C.sub.3 or C.sub.4 alkyl or alkenyl, or C.sub.1 -C.sub.4 alkyl when R.sup.2 is unsubstituted ethylene or propylene, respectively, X is --O-- or --S--, and Y and B don't form methylenedioxy, which is useful for dyeing or printing hydrophobic fiber materials with superior dyeability to give a dyed or printed product of a red color excellent in fastness properties, particularly those such as washing fastness.Type: GrantFiled: September 15, 1989Date of Patent: December 31, 1991Assignee: Sumitomo Chemical Co. Ltd.Inventors: Yasuyoshi Ueda, Jun Yamamoto, Takashi Omura, Hideo Hattori, Shinei Ikeou, Yosuke Yamamoto
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Patent number: 5004813Abstract: Chromogenic phthalides and azaphthalides of the formula ##STR1## in which V.sub.1 and V.sub.2 are each, independently of the other, hydrogen, halogen, lower alkyl, lower alkoxy, (lower alkoxy)carbonyl or --NR.sub.1 R.sub.2, at least one of the radicals V.sub.1 and V.sub.2 being lower alkoxy or --NR.sub.1 R.sub.2, A is an unsubstituted or halogen-, cyano-, nitro-, (lower alkyl)-, (lower alkoxy)-, (lower alkyl)thio-, (lower alkyl)amino- or di(lower alkyl)amino-substituted benzene, naphthalene, pyridine, quinoline, pyrazine or quinoxaline ring, B is a substituted phenyl radical of the formula ##STR2## or a 3-indolyl of the formula ##STR3## Q is ##STR4## --S-- or --O--, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each, independently of the others, hydrogen, unsubstituted or halogen-, hydroxy-, cyano- or (lower alkoxy)-substituted alkyl, cycloalkyl or unsubstituted or ringsubstituted phenalkyl or phenyl, or the substituent pairs (R.sub.1 and R.sub.2) and (R.sub.3 and R.sub.Type: GrantFiled: August 24, 1989Date of Patent: April 2, 1991Assignee: Ciba-Geigy CorporationInventors: Rox Phaff, Davor Bedekovic
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Patent number: 4876357Abstract: Chromogenic phthalides and azaphthalides of the formula ##STR1## in which V.sub.1 and V.sub.2 are each, independently of the other, hydrogen, halogen, lower alkyl, lower alkoxy, (lower alkoxy)carbonyl or --NR.sub.1 R.sub.2, at least one of the radicals V.sub.1 and V.sub.2 being lower alkoxy or --NR.sub.1 R.sub.2, A is an unsubstituted or halogen-, cyano-, nitro-, (lower alkyl)-, (lower alkoxy)-, (lower alkyl)thio-, (lower alkyl)amino- or di(lower alkyl)amino-substituted benzene, naphthalene, pyridine, quinoline, pyrazine or quinoxaline ring, B is a substituted phenyl radical of the formula ##STR2## or a 3-indolyl of the formula ##STR3## Q is ##STR4## --S-- or --O--, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each, independently of the others, hydrogen, unsubstituted or halogen-, hydroxy-, cyano- or (lower alkoxy)-substituted alkyl, cycloalkyl or unsubstituted or ringsubstituted phenalkyl or phenyl, or the substituent pairs (R.sub.1 and R.sub.2) and (R.sub.3 and R.sub.Type: GrantFiled: October 26, 1987Date of Patent: October 24, 1989Assignee: Ciba-Geigy CorporationInventors: Rox Phaff, Davor Bedekovic
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Patent number: 4868301Abstract: Oxophthalazinyl acetic acids having aldose reductase inhibitory properties of the formula ##STR1## wherein Z is hydrogen or methyl, U is S, CH.sub.2 or a covalent bond, and R.sup.1, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as herein defined, are prepared by reacting an intermediate oxophthalazinyl acetic acid ester having a cyano or alkylamido group with an aniline derivative of the formula ##STR2## Processes for the preparation of the intermediate oxophthalazinyl acetic esters are disclosed.Type: GrantFiled: March 8, 1988Date of Patent: September 19, 1989Assignee: Pfizer Inc.Inventors: Banavara L. Mylari, William J. Zembrowski
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Patent number: 4725622Abstract: A method of treating rheumatoid arthritis which method comprises administering to a mammal in need of such treatment a therapeutically effective amount of a compound of the formula: ##STR1## and the pharmaceutically acceptable salts thereof, wherein:A is oxygen or sulfur;R.sup.1 is selected from the group consisting of H, ##STR2## in which Y is oxygen or sulfur:R.sup.2 is alkyl, haloalkyl or --NR.sup.4 R.sup.5, where R.sup.4 and R.sup.5 are independently H, alkyl, haloalkyl, cycloalkyl, phenyl optionally monosubstituted with halogen, hydroxy, carboxy, chlorocarbonyl, sulfonylamino, nitro, cyano, phenyl, alkyl, acyl, alkoxycarbonyl, acylamino, dialkylamino or dialkylaminoethoxycarbonyl, phenyl optionally disubstituted with hydroxy, carboxy, nitro or alkyl, or benzyl optionally substituted with dialkylamino;n is an integer from 0-6;R.sup.3 is H alkyl or a pharmaceutically acceptable cation;Q and R are independently H or --CO.sub.2 R.sup.Type: GrantFiled: January 23, 1986Date of Patent: February 16, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Anthony C. Allison, Elsie M. Eugui, Joseph M. Muchowski
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Patent number: 4695648Abstract: A compound having a potentially inhibitory effect on 15-hydroxy-prostaglandin dehydrognase (PGDH) and having the formula ##STR1## in which R.sub.1 and R.sub.2 are hydrogen or lower alkyl;R.sub.3 is hydrogen, lower alkyl or substituted or unsubstituted phenyl;R.sub.4, R.sub.5, and R.sub.6 are hydrogen, halogen, lower alkyl, lower alkoxy, cyano, carboxy or nitro; at least one of the groups R.sub.4 to R.sub.6 being hydrogen;R.sub.7 to R.sub.11 are hydrogen, halogen, cyano, lower alkyl, trifluoromethyl, lower alkoxy, hydroxy, lower acyl, lower alkoxycarbonyl, N,N,-diloweralkyl-aminocarbonyl or N,N-loweralkylene-aminocarbonyl; and R.sub.8 and R.sub.10 may in addition be carboxy; at least two of R.sub.7 to R.sub.11 always being hydrogen; and--A-- is --CO--, --CH.sub.2 --CO--, --CH.dbd.CH--, --CH.dbd.CH--CO-- or corresponding groups in which a hydrogen atom is replaced by a lower alkyl group.The invention comprises also lactones of those compounds in which R.sub.Type: GrantFiled: August 29, 1985Date of Patent: September 22, 1987Assignee: Pharmacia ABInventors: Karl H. Agback, Tamara Agback, Alf S. Nygren
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Patent number: 4686234Abstract: Compounds useful for treating inflammatory diseases, in particular rheumatoid arthritis, represented by the formula: ##STR1## and the pharmaceutically acceptable salts thereof, wherein:R.sub.1 is H or lower alkyl having 1 to 6 carbon atoms;R.sub.2 is H, lower alkyl having 1 to 6 carbon atoms or ##STR2## in which R.sub.3 is H, lower alkyl having 1 to 6 carbon atoms or a pharmaceutically acceptable cation;R.sub.4 and R.sub.5 are each independently H or lower alkyl having 1 to 6 carbon atoms;X and Y are each independently O or S; andn is an integer of 1-6.Type: GrantFiled: November 27, 1985Date of Patent: August 11, 1987Assignee: Syntex (U.S.A) Inc.Inventors: Peter H. Nelson, Anthony C. Allison, Elsie M. Eugui
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Patent number: 4620850Abstract: A composition for oxidative dyeing of hair is disclosed, having at least one compound of the general formula ##STR1## wherein X is CH.sub.2, O, S, NH, NR', CH(OH), CHR', CH(NH.sub.2), or CH(CH.sub.3),Y is O, NH,Z is O, S, NH,R is H, OH, R', OR', NR'.sub.2, NO.sub.2, halogen, andR' is an alkyl group with one to five carbon atoms.Type: GrantFiled: August 8, 1984Date of Patent: November 4, 1986Assignee: Wella AktiengesellschaftInventors: Heinrich Bachmann, Plato Portmann
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Patent number: 4605738Abstract: Highly selective and high yield process for producing antitumor agent 1-phthalidyl-5-fluorouracil derivatives of formula (I) which comprises reacting a phthalidyl compound (II) with an amine (III) to yield the quaternary ammonium salts (IV), and reacting the latter with 5-fluorouracil. ##STR1## [wherein X is leaving group; ##STR2## is triethylamine, N-methylmorpholine, N-ethylmorpholine, and the like; R.sup.4 and R.sup.5 each is hydrogen, trialkylsilyloxy, alkoxy, nitro, cyano, carboxy, or alkoxycarbonyl].Type: GrantFiled: November 9, 1983Date of Patent: August 12, 1986Assignee: Shionogi & Co., Ltd.Inventors: Susumu Kamata, Nobuhiro Haga, Wataru Nagata, Takeaki Matsui
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Patent number: 4599445Abstract: A method is described for autoxidizing particular ortho-dialkyl substituted aromatic compounds using a particular type of solvent which gives rise to the formation of 3-alkanoyloxyphthalide compounds, some of which are novel.The phthalides in turn are ionically oxidized to their corresponding aromatic polycarboxylic acids.Combination of the two methods provides a means for converting ortho dialkyl substituted aromatic compounds directly to the corresponding polycarboxylic acids in higher yields and at generally lower overall temperatures and reaction conditions compared to prior art methods.Polycarboxylic acids so obtained are known to be useful in the preparation of alkyds, polyesters, and the like, and, particularly, in the formation of the corresponding acid anhydrides which are used in the preparation of organic high temperature polymers such as polyamides, polyamideimides, and polyimides.Type: GrantFiled: September 21, 1984Date of Patent: July 8, 1986Assignee: The Dow Chemical CompanyInventor: Visweswara R. Durvasula
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Patent number: 4567281Abstract: This invention is a process for cyclizing an ortho-alkenyl arenol, wherein the double bond of the alkenyl moiety is one or two carbons removed from the aromatic ring, with carbon monoxide, wherein the process comprises contacting an ortho-alkenyl arenol with carbon monoxide in the presence of a catalytic amount of a catalyst comprising (1) a rhodium-carbonyl complex and (2) an amine with a pK.sub.a of 6 or greater, arsine, phosphine, stibine or mixture thereof, under conditions such that a lactone-fused aromatic compound is prepared.Type: GrantFiled: June 6, 1983Date of Patent: January 28, 1986Assignee: The Dow Chemical CompanyInventor: Robert A. Dubois
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Patent number: 4562271Abstract: A method is described for autoxidizing particular ortho-dialkyl substituted aromatic compounds using a particular type of solvent which gives rise to the formation of 3-alkanoyloxyphthalide compounds, some of which are novel.The phthalides in turn are ionically oxidized to their corresponding aromatic polycarboxylic acids.Combination of the two methods provides a means for converting ortho dialkyl substituted aromatic compounds directly to the corresponding polycarboxylic acids in higher yields and at generally lower overall temperatures and reaction conditions compared to prior art methods.Polycarboxylic acids so obtained are known to be useful in the preparation of alkyds, polyesters, and the like, and, particularly, in the formation of the corresponding acid anhydrides which are used in the preparation of organic high temperature polymers such as polyamides, polyamideimides, and polyimides.Type: GrantFiled: September 21, 1984Date of Patent: December 31, 1985Assignee: The UpJohn CompanyInventor: Visweswara R. Durvasula
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Patent number: 4535090Abstract: 3,5-diphenyl-1H-1,2,4-triazoles with contragestational activity of the following formula ##STR1## wherein R may be located on one or the other of the two adjacent nitrogen atoms and may represent hydrogen or a group R.sub.5 CO-- wherein R.sub.5 is an aliphatic saturated or unsaturated hydrocarbyl containing from 1 to 20 carbon atoms, R.sub.1, R.sub.2 and R.sub.3, each independently are selected from hydrogen, lower alkyl and lower alkoxy or R.sub.2 and R.sub.3 together may represent a methylenedioxy group, and R.sub.4 is an aliphatic saturated or unsaturated hydrocarbyl group of from 1 to 20 carbons, with the proviso that when R is hydrogen or an R.sub.5 CO-- group wherein R.sub.5 contains 4 or less carbon atoms, R.sub.4 must contain 5 or more carbons.These compounds have proven to be highly effective in terminating pregnancy in several animal species after a single parenteral injection.Type: GrantFiled: October 15, 1982Date of Patent: August 13, 1985Assignee: Gruppo Lepetit S.p.A.Inventors: Giulio Galliani, Amedeo Omodei-Sale, Pietro Consonni, Alessandro Assandri
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Patent number: 4535172Abstract: This invention relates to 3-aryl or heteroaryl-3-alkoxy, phenoxy-, alkylthio- or phenylthiophthalides useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared by the interaction of 2-(disubstituted amino)phenylcarbonylbenzoic acids with an acid chloride or an anhydride of an alkanoic acid in the first step and a further reaction of the product of the first step with an alcohol, a thioalcohol, a phenol or a thiophenol in a second step.Type: GrantFiled: January 8, 1982Date of Patent: August 13, 1985Assignee: The Hilton-Davis Chemical Co.Inventors: Paul J. Schmidt, William M. Hung
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Patent number: 4485247Abstract: A method is described for autoxidizing particular ortho-dialkyl substituted aromatic compounds using a particular type of solvent which gives rise to the formation of 3-alkanoyloxyphthalide compounds, some of which are novel.The phthalides in turn are ionically oxidized to their corresponding aromatic polycarboxylic acids.Combination of the two methods provides a means for converting ortho dialkyl substituted aromatic compounds directly to the corresponding polycarboxylic acids in higher yields and at generally lower overall temperatures and reaction conditions compared to prior art methods.Polycarboxylic acids so obtained are known to be useful in the preparation of alkyds, polyesters, and the like, and, particularly, in the formation of the corresponding acid anhydrides which are used in the preparation of organic high temperature polymers such as polyamides, polyamideimides, and polyimides.Type: GrantFiled: January 24, 1983Date of Patent: November 27, 1984Assignee: The Upjohn CompanyInventor: Visweswara R. Durvasula
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Patent number: 4483867Abstract: Novel antifibrinolytically active compounds of the formula ##STR1## and therapeutically acceptable salt thereof, whereinR.sup.1 is selected from the group consisting of(a) alkyl groups containing 1-4 carbon atoms,(b) alkoxy groups containing 1-4 carbon atoms, ##STR2## R.sup.2 is selected from the group consisting of (a) H,(b) alkyl groups containing 1-4 carbon atoms,(c) --COOR.sup.3, wherein R.sup.3 is an alkyl group containing 1-4 carbon atoms,(d) --CONR.sup.4 R.sup.5, wherein R.sup.4 and R.sup.5 are the same or different alkyl groups containing 1-3 carbon atoms;or wherein R.sup.1 and R.sup.Type: GrantFiled: November 10, 1982Date of Patent: November 20, 1984Assignee: KabiVitrum ABInventors: Carl M. E. Svahn, Ferenc Merenyi, Lennart E. Karlsson, Gunnar Hanshoff
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Patent number: 4459414Abstract: Novel tetrasubstituted phthalic acid derivatives of the formula ##STR1## are described, in which Y.sub.1 and Y.sub.2 are oxygen and Y is ##STR2## or --O--, or one of Y.sub.1 and Y.sub.2 is oxygen and the other is .dbd.N--R" and Y is --O--, and m, n, X, R, R' and R" are as defined in claim 1. The compounds (I) are suitable as sensitizers for photocrosslinkable polymers or as initiators for the photopolymerization of ethylenically unsaturated compounds or for the photochemical crosslinking of polyolefins.Type: GrantFiled: March 29, 1982Date of Patent: July 10, 1984Assignee: Ciba-Geigy CorporationInventors: Walter Fischer, Hans Zweifel
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Patent number: 4439610Abstract: A process is described for preparing triarylmethane derivatives of a high purity in an extremely high yield from 3-phenylphthalide derivatives and aniline derivatives or indole derivatives with Friedel-Crafts type catalyst or Friedel-Crafts type catalyst and an oxidizing agent.Type: GrantFiled: March 4, 1977Date of Patent: March 27, 1984Assignee: Kanzaki Paper Manufacturing Company, Ltd.Inventors: Mitsuru Kondo, Kiyoshi Yasui, Makoto Miyake, Hiroshi Iwasaki, Tetsuo Shiraishi
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Patent number: 4416826Abstract: Peresters of the formula: ##STR1## wherein R is an alkyl group; and ##STR2## light-absorbing chromophore group; and use thereof as photoinitiators are provided.Type: GrantFiled: October 29, 1980Date of Patent: November 22, 1983Inventor: Douglas C. Neckers
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Patent number: 4362880Abstract: An improved process for the preparation of 3-substituted thiophenes. The thiophenes are useful for the preparation of penicillins and cephalosporins.The process is for the preparation of a thiophene of formula (I): ##STR1## where R.sup.1 represents a carboxylic acid group, or an ester or amide thereof or a nitrile group; R.sup.2 represents a group suitable for use as an .alpha.-substituent in the side-chain of a penicillin or cephalosporin; which comprises treating under basic conditions a compound of formula (II): ##STR2## wherein X represents halogen or optionally functionalized hydroxyl, Y represents halogen, hydroxyl, or alkoxy; with a source of nucleophilic sulphur ionically bound to a polymeric support.Type: GrantFiled: March 30, 1981Date of Patent: December 7, 1982Assignee: Beecham Group LimitedInventors: Kenneth T. Veal, Trevor J. Grinter