The Other Cyclo Of The Bicyclo Ring System Is Benzene (e.g., Phthalides, Etc.) Patents (Class 549/307)
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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: 5169976Abstract: Variously substituted 4-(biphen-2-ylmethylcarbamoyl)-3-hydroxybutyric acids and esters, also named as N-(biphen-2-yl)-3-hydroxyglutaramic acid derivatives, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.Type: GrantFiled: May 3, 1990Date of Patent: December 8, 1992Assignee: Pfizer Inc.Inventor: Peter A. McCarthy
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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: 5073192Abstract: Phenoxy phthalide derivatives having the general 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; R.sub.4 represents a saturated alkyl group; R.sub.5 represents an unsaturated alkyl group; and X represents an oxygen or sulphur atom, are useful as herbicides.Type: GrantFiled: October 2, 1990Date of Patent: December 17, 1991Assignee: Shell Internationale Research Maatschappij B.V.Inventors: Michael T. Clark, Ian J. Gilmore
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Patent number: 5011975Abstract: A (trans 1-propenyl)disulfide derivative having a distinguished anti-tumor effect, represented by the following general formula: ##STR1## , wherein R is a lower alkylene group and R' is a hydrogen atom or a carboxyl protective group, is prepared by allowing a carboxylic acid thiol derivative, represented by the following general formula:AS--R--COOR', wherein R and R' have the same meanings as defined above and A is a thiol protective group releasable by a halogenating agent, to react with a trans 1-propenethiol derivative represented by the following general formula: ##STR2## , wherein A has the same meanings as defined above, in the presence of a halogenating agent.Type: GrantFiled: July 17, 1989Date of Patent: April 30, 1991Assignee: Nippon Miktron LimitedInventors: Tokiyuki Hiramitsu, Ken-ichi Sakamoto
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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: 4981970Abstract: Coloring phthalide compounds having general formula [I], a method of producing the phthalide compounds and a recording material comprising as a coloring component any of the coloring phthalide compounds, are disclosed, ##STR1## wherein R.sup.1 and R.sup.2 each represent a straight chain or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group, or a benzyl group, and R.sup.1 and R.sup.2 in combination may form a ring; R.sup.3 represents and alkyl group having 1 to 4 carbon atoms; R.sup.4 represents a dialkylamino group having 1 to 6 carbon atoms, a cyclic amino group or halogen; l is an integer of 0 to 4; A represents ##STR2## wherein R.sup.5 and R.sup.6 each represent a straight chain or branched alkyl group having 1 to 8 carbon atoms, a cycloalkyl group, or a benzyl group, R.sup.5 and R.sup.6 in combination may form a ring; and B is the same as A, or represents a phenyl group which may have a substituent.Type: GrantFiled: August 16, 1989Date of Patent: January 1, 1991Assignee: Ricoh Company, Ltd.Inventors: Kiyotaka Iiyama, Kunio Hayakawa
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Patent number: 4973713Abstract: A process for the production of esters or lactones, comprising reacting in the presence of a catalyst and under hydrogenation conditions hydrogen and an acyclic or cyclic carboxylic anhydride to produce the corresponding ester or lactone, wherein the catalyst is a supported catalyst comprising:(a) a group VIII metal, Re and Fe;(b) a group VIII metal on TiO.sub.2 ;(c) Ru and at least one of Re, Ag or Cu; or(d) Pd and Fe.Preferably, the anhydride has the formula ##STR1## and is reacted to form an ester of the formula ##STR2## or a lactone of the formula ##STR3## wherein R and R.sup.1 independently are lower alkyl or cycloalkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5 independently are hydrogen, lower alkyl, cycloalkyl or aryl; and wherein R.sup.3 and R.sup.4 taken together may form a saturated or unsaturated ring, or an aromatic ring. The more preferred starting material is phthalic anhydride.Type: GrantFiled: November 28, 1989Date of Patent: November 27, 1990Assignee: E. I. du Pont de Nemours and CompanyInventor: William H. Manogue
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Patent number: 4962206Abstract: A process for the production of 4-bromophthalic anhydride which comprises the reaction of 4-chlorotetrahydrophthalic anhydride with elemental bromine, in the presence of a catalytically effective amount of iron or an iron salt is disclosed.Type: GrantFiled: November 20, 1989Date of Patent: October 9, 1990Assignee: Occidental Chemical CorporationInventors: Mary K. Cocoman, Willis T. Schwartz
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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: 4849428Abstract: The present invention involves compounds having the structure: ##STR1## (a) --A-- is selected from the group consisting of ##STR2## (b) --Y is selected from certain low molecular weight moieties which terminate in specific functional groups: --C.tbd.CH, ##STR3## and aldehydes in the form of their acetals; pharmaceutical compositions comprising such compounds; and methods for treating inflammation by administering such compounds.Type: GrantFiled: November 23, 1987Date of Patent: July 18, 1989Assignee: The Procter & Gamble CompanyInventors: Roy L. M. Dobson, Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
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Patent number: 4704458Abstract: Disclosed herein is an improved process for preparing 1RS-3'RS epimer of aminated phthalideisoquinolines represented by the general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen atom or a lower alkoxy group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently hydrogen atom, amino group or a lower alkoxy group with at least one of R.sup.3 -R.sup.6 being amino group, and R.sup.7 is a lower alkyl group. The improvement comprises, after having reduced a mixture of epimers of corresponding nitro compounds of the general formula (I) wherein the amino group is replaced by nitro group into the amino compounds (I), treating said amino compound at a temperature in the range of 20.degree.-100.degree. C. in an aliphatic lower alcohol in the presence of an alkali to epimerize 1RS-3'SR epimer of said amino compound into said 1RS-3'RS epimer thereof.Type: GrantFiled: January 23, 1985Date of Patent: November 3, 1987Assignee: Mitsubishi Chemical Industries LimitedInventors: Yoshiyuki Takeda, Osamu Kawashima, Shiro Furukawa, Yasukazu Ogino
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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: 4595768Abstract: Process comprises the combination of the three steps of condensing 3-N(R).sub.2 -4-X-benzoic acid with an aromatic or heterocyclic aldehyde, Y-CHO, under acidic conditions to produce 3-Y-5-X-6-N(R).sub.2 phthalide (II), condensing said phthalide with a compound of the formula Z-H under alkaline or acid conditions to produce 2-(.alpha.-Y-.alpha.-Z)methyl-4-X-5-N(R).sub.2 benzoic acid (III), and oxidizing said benzoic acid to produce 3-Y-3-Z-5-X-6-N(R).sub.2 phthalide (I) where: R is hydrogen, non-tertiary alkyl of one to four carbon atoms, benzyl or substituted benzyl; X is hydrogen or halo; Y is 4-R.sup.1 -3-R.sup.2 -2-R.sup.1 -phenyl, 1-R.sup.5 -2-R.sup.6 -5/6-R.sup.4 -3-indolyl, 9-R.sup.7 -3-carbazolyl, 9-julolidinyl, 3,4-dioxymethylenephenyl, 2-thienyl, 1-R.sup.8 -2-pyrrolyl, or 4-pyridinyl; and Z is 4-R.sup.1 -3-R.sup.2 -2-R.sup.1 -phenyl, 1-R.sup.5 -2-R.sup.6 -5/6-R.sup.4 -3-indolyl or 1-R.sup.Type: GrantFiled: April 23, 1984Date of Patent: June 17, 1986Assignee: The Hilton-Davis Chemical Co.Inventors: Paul J. Schmidt, Nathan N. Crounse
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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: 4528385Abstract: The present invention relates to the hydrogenation of phthalic acid anhydride to phthalide. A nickel catalyst of low nickel content is used as hydrogenation catalyst, and a benzoic acid alkyl ester as solvent. Small amounts of an alkanol can be added to the benzoic acid ester. On the basis of these specific conditions, the formation of by-products such as toluylic or phthalic acids in the hydrogenation is greatly diminished, and phthalide yields are obtained which, if the preferred conditions are maintained, can amount to as much as 90%.Type: GrantFiled: January 18, 1983Date of Patent: July 9, 1985Assignee: Dynamit Nobel AGInventors: Helmut aus der Funten, Wilhelm Vogt
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Patent number: 4514415Abstract: The invention relates to novel lactones, especially benzofuranones of the general formula ##STR1## in which R.sub.1 represents hydrogen or an aliphatic radical, R.sub.2 represents an amino group di-substituted by two monovalent hydrocarbon radicals, and the aromatic ring A may be additionally substituted, and their salts and/or isomers, processes for the manufacture of compounds of the formula (I) and their salts and isomers, pharmaceutical preparations containing these compounds, and their use as the active ingredients of medicaments and/or for the manufacture of pharmaceutical preparations.Type: GrantFiled: October 21, 1982Date of Patent: April 30, 1985Assignee: Ciba Geigy CorporationInventors: Paul Wenk, Werner Breitenstein, Marcus Baumann
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Patent number: 4485246Abstract: The rate of selective hydrogenation of carboxylic acid anhydrides to esters or lactones in the presence of a ruthenium organophosphorous catalyst which contains or liberates a hydrogen halide during the hydrogenation, is improved by providing in the reaction medium prior to or during the hydrogenation a basic amino compound to remove the hydrogen halide.Type: GrantFiled: October 29, 1982Date of Patent: November 27, 1984Assignee: Sun Tech, Inc.Inventor: James E. Lyons
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Patent number: 4485245Abstract: Process for selective homogeneous catalytic hydrogenation of carboxylic acid anhydrides to ester or lactones at an improved rate and to obtain improved yields wherein the catalyst is a ruthenium trichlorostannate complex of the formula: ##STR1## wherein X is hydrogen, chlorine, bromine, iodine or lower alkyl; m is the integer 1 or 2; n is an integer of from 0 to 3 but when n is 2 or 3, X may be the same or different; M is P, As or Sb; R.sup.6, R.sup.7 and R.sup.8 independently are lower alkyl, cycloalkyl, aryl, benzyl or a bidentate legand; x is an integer of from 1 to 4 but when x is 2 or more, M may be the same or different; L is a neutral ligand, olefin, CO or (R.sup.9).sub.2 CO wherein R.sup.9 is lower alkyl; y is an integer of from 0 to 3 but when y is 2 or 3, L may be the same or different; and the sum of x and y is at least 2.Type: GrantFiled: October 29, 1982Date of Patent: November 27, 1984Assignee: Sun Tech, Inc.Inventors: Chao-Yang Hsu, James E. Lyons
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Patent number: 4477675Abstract: The process of preparing a compound of the formula: ##STR1## wherein, Y and Z are each H, alkyl, halo, alkoxy, trifluoromethyl, hydroxy, alkanoyloxy, or alkanoylamino;X is F, Cl, Br, or NR.sub.1 R.sub.2 wherein R.sub.1 and R.sub.2 are each hydrogen, alkyl, alkynyl, alkenyl, cycloalkyl, aryl or aralkyl; andR is H, alkyl, cycloalkyl, or aralkyl; which comprises the step of oxidation of the corresponding 3-desoxy compound.Type: GrantFiled: September 7, 1982Date of Patent: October 16, 1984Assignee: USV Pharmaceutical CorporationInventors: Joseph Auerbach, Frederick A. Golec, Jr.
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Patent number: 4446327Abstract: A process is provided for the direct hydrolysis of pentachloro-o-xylene to 3-chlorophthalide in high yield and high purity by carrying out the hydrolysis with 2 mols of water in the presence of a catalyst at a temperature above 100.degree. C., proportioning the water uniformly during the reaction time so that it immediately reacts completely and does not leave the reaction vessel in vapor form.Type: GrantFiled: May 6, 1982Date of Patent: May 1, 1984Assignee: Dynamit Nobel AktiengesellschaftInventors: Greger Weisgerber, Klaus-Dieter Steffen
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Patent number: 4371542Abstract: What are disclosed are prostacylin PGI.sub.2 analogs of the formula ##STR1## having a more specific or longer lasting pharmacological action than PGI.sub.2, methods of making these analogs; and methods and pharmaceutical preparations for inhibiting blood platelet aggregation, for treating hypertension, for the treatment or prophylaxis of gastrointestinal ulcers, and for the treatment of asthma.Type: GrantFiled: February 20, 1981Date of Patent: February 1, 1983Assignee: Hoechst AktiengesellschaftInventors: Gerhard Beck, Jochen Knolle, Richard H. Rupp, Bernward Scholkens
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Patent number: 4367238Abstract: This invention relates to new phenyl-alkanoic acids, their derivatives at the carboxy group, and pharmaceutically acceptable salts thereof, which have anti-inflammatory, analgesic and antipyretic activities.Type: GrantFiled: January 21, 1981Date of Patent: January 4, 1983Assignee: Fujisawa Pharmaceutical Company, Ltd.Inventors: Ikuo Ueda, Yoshihiko Kitaura, Masaaki Matsuo, Nobukiyo Konishi
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Patent number: 4331600Abstract: Compounds of the formula ##STR1## wherein, Y and Z are each H, alkyl, halo, alkoxy, trifluoromethyl, hydroxy, alkanoyloxy, or alkanoylamino;X is F, Cl Br or NR.sub.1 R.sub.2 in which R.sub.1 and R.sub.2 are each hydrogen, alkyl, alkenyl, alkynyl, aryl, aralkyl or cycloalkyl; andR is H, alkyl, cycloalkyl or aralkyl; and salts thereof.The compounds have utility as anti-hypertensive and diuretic agents and as intermediates for the preparation of other anti-hypertensive and diuretic agents.Type: GrantFiled: October 31, 1980Date of Patent: May 25, 1982Assignee: USV Pharmaceutical CorporationInventors: Frederick A. Golec, Jr., Joseph Auerbach