Oxy In Acid Moiety Patents (Class 560/53)
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Patent number: 4912235Abstract: This invention relates to a process for making a compound of formula I ##STR1## in the form of a stereoisomer or mixture thereof, wherein R is hydrogen, lower alkyl; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta., or a pharmaceutically acceptable, non-toxic salt of the compound wherein R is hydrogen; novel intermediates useful for preparing these compounds; processes for making the intermediates; and a stereoisomer of the compound of formula I wherein R is methyl and X is hydrogen and a process for making same.Type: GrantFiled: June 7, 1988Date of Patent: March 27, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Gary F. Cooper, Douglas L. Wren, Albert R. Van Horn, Tsung-Tee Li, Colin C. Beard
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Patent number: 4898877Abstract: Novel circulation-active cyclohexenecarboxylates of the formula ##STR1## in which R.sup.1 is an organic radical,R.sup.2 is an optionally substituted aryl radical,R.sup.3 is an optionally substituted alkyl or aryl radical,X and Y are --CN, --COR.sup.4, --SO.sub.2 R.sup.4, --COOR.sup.5, --CONR.sup.6 R.sup.7 or --SO.sub.2 NR.sup.6 R.sup.7, andR.sup.4, R.sup.5, R.sup.6 and R.sup.7 are various organic radicals.Type: GrantFiled: February 18, 1988Date of Patent: February 6, 1990Assignee: Bayer AktiengesellschaftInventors: Horst Meyer, Eckhard Schwenner, Martin Bechem, Rainer Gross, Matthias Schramm, Michael Kayser, Siegbert Hebisch
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Patent number: 4889947Abstract: Sunscreen compositions are described which contain certain substituted naphthalenylidenes which act as UV filters when incorporated in a carrier in amounts ranging from 0.1-50% by weight.Type: GrantFiled: July 28, 1988Date of Patent: December 26, 1989Assignee: ICI Americas Inc.Inventors: Charalambos J. Phalangas, Thomas P. Cleary
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Patent number: 4888423Abstract: 6-(4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinones of formula I ##STR1## where R.sub.1 and R.sub.2 are independently alkyl, cycloalkyl, aryl or aralkyl, R.sub.3 and R.sub.4 are independently hydrogen or alkyl, n is 1 to 4 and T is hydrogen, alkyl, substituted alkyl, alkylene or arylene, are effective in stabilizing organic materials against oxidative, thermal and actinic degradation.Type: GrantFiled: October 6, 1986Date of Patent: December 19, 1989Assignee: Ciba-Geigy CorporationInventors: Paul A. Odorisio, Steven D. Pastor
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Patent number: 4888358Abstract: Novel 13,14-dihydroprostaglandin derivatives of the formula ##STR1## wherein: m is 1 or 3;R.sub.1 is hydrogen or alkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 and R.sub.4 are independently hydrogen or methyl;R.sub.5 is alkyl, CF.sub.3 (CH.sub.2).sub.n -- in which n is an integer of 3-5, cycloalkyl, or optionally substituted phenyl, benzyl or phenoxy; orR.sub.4 and R.sub.5 taken together with the carbon to which they are attached is cycloalkyl of 4-8 carbon atoms;X is cis --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 -- when m is 3, orX is --CH.sub.2 CH.dbd.C.dbd.CH-- when m is 1;and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta.;or a pharmaceutically acceptable salt thereof,have been prepared. They are useful in particular for their antihypertensive and anti-ulcerogenic properties.Type: GrantFiled: August 25, 1988Date of Patent: December 19, 1989Assignee: Syntex (U.S.A.) Inc.Inventors: Joan Huguet, Joseph M. Muchowski, Maria T. Lara
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Patent number: 4873363Abstract: A new process for the preparation of a 3-(4'-bromobiphenyl-4-yl)tetralin-1-one known as a key intermediate for the production of rodenticides and clinical medicines is provided. The title compound is prepared from P-bromobiphenylbenzylketone in three steps, wherein one of key inventions is dehydroxylation of 3-(4'-bromobiphenyl)-3-hydroxy-4-phenylbutyric acid ethyl ester using trialkylsilane in trifluoroacetic acid. This new process offers a high yield with a facile way and is more suitable for a commercial production than the prior art methods.Type: GrantFiled: May 11, 1988Date of Patent: October 10, 1989Assignee: Korea Advanced Institute of Science and TechnologyInventors: In O. Kim, Sang G. Lee
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Patent number: 4871756Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4, E.sub.4 and the slow reacting substance of anaphylaxis.As such, these compounds will be useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.Type: GrantFiled: February 17, 1987Date of Patent: October 3, 1989Assignee: Merck Frosst Canada, Inc.Inventors: John Gillard, Joshua Rokach, Patrice C. Belanger
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Patent number: 4870199Abstract: Process for the synthesis of compounds of the formula ##STR1## in R[R*,S*] enantiomeric form, wherein each P.sub.1 is independently an hydroxy group-protecting group, andR.sub.2z is C.sub.1-4 alkyl, benzyl or allyl,comprising, as a key step when R.sub.2z is R.sub.2x, the reaction of the compound of the formula ##STR2## in (S) enantiomeric form with a compound of the formulaMg.sup. .circle.+2 (.sup..crclbar. OOC--CH.sub.2 --COOR.sub.2x).sub.2to obtain a compound of the formula ##STR3## in (S) enantiomeric form, and, as a key step when R.sub.2z is R.sub.2y, the reaction of a compound of the formula ##STR4## in (S) enantioimeric form with a compound of the formulaLi.sup..sym..crclbar. CH.sub.2 --COOR.sub.2yto obtain a compound of the formula ##STR5## in (S) enantiomeric form, wherein R.sub.2x is primary or secondary C.sub.1-4 alkyl, benzyl or allyl,R.sub.2y is C.sub.1-4 alkyl not containing an asymmetric carbon atom, andR.sub.Type: GrantFiled: March 10, 1988Date of Patent: September 26, 1989Assignee: Sandoz Pharm. Corp.Inventors: Kau-Ming Chen, Goetz E. Hardtmann, Prasad K. Kapa, George T. Lee, Jerome Linder, Sompong Wattanasin
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Patent number: 4867737Abstract: Compounds of the formula (I): ##STR1## in which R.sub.1 represents alkoxy containing from 1 to 8 carbon atoms, and R represents hydrogen or alkyl containing from 1 to 8 carbon atoms, as well as their alkali metal, alkaline-earth metal, ammonium or amine salts, which are useful in the treatment of hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity. Also, therapeutic compositions containing the same and method of treating patients suffering from these ailments.Type: GrantFiled: June 21, 1988Date of Patent: September 19, 1989Assignee: Roussel UCLAFInventors: Fernando Barzaghi, Alina Butti
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Patent number: 4866201Abstract: A new compound is provided by a cyclohexane derivative of the formula ##STR1## wherein R represents a hydrogen atom or an alkyl group, an alkylthioalkyl group or an unsubstituted or substituted phenyl group; and R.sup.1 represents an alkyl group, an unsubstituted or substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt of said cyclohexane compound.This cyclohexane compound exhibits useful plant-growth regulating effects on crop-plants and also non-crop plants such as lawn and may be prepared by cyclization of an acetonylsuccinic acid dialkyl ester, followed by reaction with an organic acid chloride and by intermolecular rearrangement.Type: GrantFiled: July 7, 1987Date of Patent: September 12, 1989Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
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Patent number: 4855292Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.Type: GrantFiled: July 23, 1987Date of Patent: August 8, 1989Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
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Patent number: 4853398Abstract: This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.Type: GrantFiled: April 13, 1987Date of Patent: August 1, 1989Assignee: Eli Lilly and CompanyInventors: F. P. Carr, Robert D. Dillard, Doris E. McCullough
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Patent number: 4851523Abstract: Compounds of the general formula (1) ##STR1## in which n is 1 or 2;m is 2-5 and X is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --; or m is 1-4 and X is --CH.dbd.C.dbd.CH--;R.sup.1 is phenyl, substituted phenyl or naphthyl;Y is substituted or unsubstituted 3-phenoxy-2-hydroxypropyl.These compounds inhibit gastric acid secretion and provide gastrointestinal cytoprotection, and may be formulated for use in the treatment of ulcers.Type: GrantFiled: October 21, 1987Date of Patent: July 25, 1989Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Harry Finch
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Patent number: 4847369Abstract: Compounds are described of formula (1) ##STR1## wherein m is 1 to 4;n is zero, 1 or 2;p is 1 to 4;Z is a group CO.sub.2 R.sup.1 where R.sup.1 is(a) a hydrogen atom or an alkyl, phenalkyl or 2-naphthyl group;(b) phenyl or substituted phenyl;(c) --CH.sub.2 COR.sup.5 where R.sup.5 is phenyl substituted phenyl or 2-naphthyl;or Z is --CH.sub.2 OH, --CHO or CONHR.sup.9 [where R.sup.9 is a hydrogen atom or alkyl, aryl, --COR.sup.10 (where R.sup.10 is a hydrogen atom or an alkyl or aryl group) Or --SO.sub.2 R.sup.11 (where R.sup.11 is an alkyl or aryl group)];Y is substituted or unsubstituted 3-phenoxy-2-hydroxypropyl.These compounds inhibit gastric acid secretion and provide gastrointestinal cytoprotection, and may be formulated for use in the treatment of ulcers.Type: GrantFiled: October 21, 1987Date of Patent: July 11, 1989Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Harry Finch, Duncan B. Judd, James D. Meadows
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Patent number: 4845264Abstract: A novel phenoxycarboxylic acid of formula (I) is disclosed. The compound is effective as herbicide for eradicating broad-leaved weeds. A combination of the phenoxycarboxylic acid and a N-phosphonomethylglycine or a glufosinate which is known as a herbicide is very effective for eradicating both broad-leaved weeds and narrow-leaved weeds.Type: GrantFiled: March 1, 1988Date of Patent: July 4, 1989Assignee: Teijin LimitedInventors: Shizuo Azuma, Toshiyuki Hiramatsu, Koji Nakagawa, Yataro Ichikawa
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Patent number: 4845248Abstract: There are disclosed intermediate which can be converted into podophyllotoxin and related compounds, which are known antineoplastic agents. There are also disclosed processes for the preparation of such intermediates, and processes for the conversion of the intermediates into known intermediates which are readily converted into podophyllotoxin and related compounds.Type: GrantFiled: December 7, 1987Date of Patent: July 4, 1989Assignee: Bristol-Myers CompanyInventors: Takushi Kaneko, Henry S. L. Wong
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Patent number: 4845282Abstract: The present invention provides an industrially very advantageous process for producing prostaglandins E.sub.1 with fewer steps and in higher yield. The process comprises reacting a 7-hydroxyprostaglandin E with a reactive derivative of an organic sulfonic acid in the presence of a basic compound to form the corresponding 7-organic sulfonyloxyprostaglandin E, treating the resulting 7-organic sulfonyloxyprostaglandin E, after or without isolation, in the presence of a basic compound to form a .DELTA..sup.7 -prostaglandin E, thereafter selectively reducing the carbon-carbon unsaturated bond existing on the .alpha.-chain. Some of the 7-hydroxyprostaglandins E and .DELTA..sup.7 -prostaglandins E used in the process are novel compounds.Type: GrantFiled: January 21, 1988Date of Patent: July 4, 1989Assignee: Teijin LimitedInventors: Ryoji Noyori, Masaaki Suzuki, Toshio Kawagishi, Seizi Kurozumi
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Patent number: 4840951Abstract: Naphthalene derivative of the formula: ##STR1## wherein Ring A is a substituted or unsubstituted benzene ring; each of R.sup.1 and R.sup.2 is a group of the formula: --OR.sup.5, --NHR.sup.5 or ##STR2## or either one of R.sup.1 and R.sup.2 is a lower alkoxy group and the other one is a group of the formula: --OR.sup.5, --NHR.sup.5 or ##STR3## each of R.sup.3 and R.sup.4 is a lower alkoxy group, or one of R.sup.3 and R.sup.4 is a lower alkoxy group and the other is a hydrogen atom; R.sup.5 is a substituted alkyl group, a heterocyclic group, a cycloalkyl group, an alkyl group of at least 5 carbon atoms or alkenyl group; and each of R.sup.6 and R.sup.7 is hydrogen atom or a lower alkyl group and salts thereof are disclosed. Said naphthalene derivative (I) and its salts have excellent hypolipidemic activity and are useful for treatment or prophylaxis of hyperlipidemia and/or arteriosclerosis.Type: GrantFiled: June 17, 1987Date of Patent: June 20, 1989Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Tameo Iwasaki, Kohki Takashima
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Patent number: 4837363Abstract: Compounds are described of formula (1) ##STR1## in which n is 1 or 2;m is 2-5 and X is --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 --, or m is 1-4 and X is --CH.dbd.C.dbd.CH--;R.sup.1 is --H, C.sub.1-6 alkyl or C.sub.7-10 phenalkyl,Y substituted or unsubstituted 3-phenoxy-2-hydroxypropyl,and their salts.These compounds inhibit gastric acid secretion and provide gastrointestinal cytoprotection, and may be formulated for use in the treatment of ulcers.Type: GrantFiled: April 23, 1985Date of Patent: June 6, 1989Assignee: Glaxo Group LimitedInventor: Eric W. Collington
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Patent number: 4831190Abstract: There are disclosed 2,4,5-Trifluoro-3-hydroxybenzoic acid represented by the following formula (I): ##STR1## and a salt thereof and a process for preparing the same. Further, there is disclosed a process for preparing 3,5,6-trifluoro-4-hydroxyphthalic acid, which is employed for preparing the above compound.Type: GrantFiled: November 27, 1987Date of Patent: May 16, 1989Assignee: UBE Industries, Ltd.Inventors: Kikuo Ataka, Masayoshi Oku
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Patent number: 4829091Abstract: An improved method for the decarbalkoxylation of alkylated .beta.-keto esters to obtain high yields of ketones. In accordane with the method, decarbalkoxylation of alkylated .beta.-keto esters is accomplished by heating the esters in the presence of dilute aqueous alkali and an effective amount of a phase-transfer agent. The method produces commercially practical yields of ketone in a manner which is facile, economical and environmentally safe. Novel methylene-linked pyrethroid ketones produced from the improved method exhibit insecticidal activity against various agricultural pests.Type: GrantFiled: May 27, 1987Date of Patent: May 9, 1989Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Frank D. Mills, Richard T. Brown, Giles D. Mills, Jr
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Patent number: 4826982Abstract: Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen atom or lower alkyl group; the hydrates or the pharmaceutically acceptable acid addition or alkali salts thereof are useful as an antibacterial agent.Type: GrantFiled: September 2, 1986Date of Patent: May 2, 1989Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Kuniyoshi Masuzawa, Seigo Suzue, Keiji Hirai, Takayoshi Ishizaki
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Patent number: 4824993Abstract: Compounds are described of formula (I) ##STR1## in which n is 1 or 2;m is 2-5 and X is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --; or m is 1-4 and X is --CH.dbd.C.dbd.CH--;R.sup.1 is --H, alkyl, phenalkyl, phenyl, substituted phenyl or naphthyl;Y substituted or unsubstituted 3-phenoxy-2-hydroxypropyl.These compounds inhibit gastric acid secretion and provide gastrointestinal cytoprotection, and may be formulated for use in the treatment of ulcers.Type: GrantFiled: September 11, 1987Date of Patent: April 25, 1989Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Harry Finch, Duncan B. Judd
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Patent number: 4814487Abstract: The synthesis of amido substituted naphthalenes and their intermediates is described. The intermediates and amido substituted naphthalenes are useful as anti-inflammatory agents.Type: GrantFiled: May 7, 1987Date of Patent: March 21, 1989Assignee: Ortho Pharmaceutical CorporationInventors: William V. Murray, Michael P. Wachter
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Patent number: 4808338Abstract: Intermediate compounds of the formula ##STR1## wherein X is oxy, thio, sulfinyl or sulfonyl; R is halogen; C.sub.1 C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; trifluoromethyl or difluoromethyl; R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, or phenyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene; R.sup.3 hydrogen, C.sub.1 C.sub.4 alkyl, or phenyl with the proviso that R.sup.1 and R.sup.3 are not both phenyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or phenyl; R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.Type: GrantFiled: February 1, 1988Date of Patent: February 28, 1989Assignee: Stauffer Chemical CompanyInventor: David L. Lee
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Patent number: 4804760Abstract: A process for the preparation of a compound of the formula ##STR1## in which Y is a nitrile group, an ester group COOR.sup.1 or an acid amide CONR.sup.2 R.sup.3,R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.3 may also be phenyl, andX.sup.2, X.sup.3, X.sup.4 and X.sup.5 each independently is hydrogen, halogen, nitro, cyano, alkyl having 1-3 carbon atoms, alkoxy having 1-3 carbon atoms, alkylmercapto having 1-3 carbon atoms, alkyl-sulphonyl having 1-3 carbon atoms, or a phenylsulphonyl group which is optionally substituted in the aryl radical,comprising reacting an aminoacrylate of the formulain whichX.sup.1 is halogen, a nitro group, an alkoxy, alkoxy, alkylmercapto or alkylsulphonyl group having 1-3 carbon atoms in each case, or an arylsulphonyl group,W is hydrogen or a --CH.sub.2 CH.sub.2 Z radical,Z is a nitrile group, an ester group COOR.sup.4 or an acid amide group CONR.sup.5 R.sup.6, andR.sup.4, R.sup.5 and R.sup.6 each independently is hydrogen or C.Type: GrantFiled: April 28, 1987Date of Patent: February 14, 1989Assignee: Bayer AktiengesellschaftInventors: Michael Schriewer, Klaus Grohe
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Patent number: 4797506Abstract: 6-substituted prostaglandins E.sub.1 which are compounds represented by the following formula [I] or their enantiomers or mixtures whereof in any ratio: ##STR1## wherein R.sup.1 represents a hydrogen atom, a C.sub.1 -C.sub.16 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenyl C.sub.3 -C.sub.10 cycloalkyl group, a substituted or unsubstituted phenyl (C.sub.1 -C.sub.2) alkyl group, or one equivalent cation; R.sup.2 and R.sup.3, which may be the same or different, represent a hydrogen atom, a tri (C.sub.1 -C.sub.7) hydrocarbon silyl group, or a group forming an acetal linkage together with an oxygen atom of a hydroxyl group; R.sup.4 represents a hydrogen atom, a methyl group or a vinyl group; R.sup.5 represents a linear or branched C.sub.3 -C.sub.8 alkyl group, a linear or branched C.sub.3 -C.sub.8 alkenyl group, a linear or branched C.sub.3 -C.sub.8 alkynyl group, a phenyl group which may be substituted, a phenoxy group which may be substituted, a C.sub.3 -C.sub.Type: GrantFiled: October 18, 1985Date of Patent: January 10, 1989Assignee: Teijin LimitedInventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi
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Patent number: 4797391Abstract: The invention relates to novel [(5,6-dichloro-3-oxo-9,9a-disubstituted-2,3,9,9a-tetrahydro-fluoren-7-yl)o xy]alkanoic acids and alkanimidamides, 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, various brain concussions and elevated intracranial pressure.Type: GrantFiled: February 8, 1988Date of Patent: January 10, 1989Assignee: Merck & Co., Inc.Inventors: Otto W. Woltersdorf, Jr., Edward J. Cragoe, Jr., Adolph M. Pietruszkiewicz
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Patent number: 4795819Abstract: There is provided a novel and efficient stereoselective total synthesis of epipodophyllotoxin and related epipodophyllotoxin compounds of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each are independently hydrogen or (lower)alkoxy, or R.sup.1 and R.sup.2, taken together, is methylenedioxy; R.sup.4 and R.sup.6 each are independently hydrogen or (lower)alkoxy; and R.sup.5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof. The present invention also provides novel intermediates and processes for the preparation of said intermediates, which are then converted into known antineoplastic agents.Type: GrantFiled: July 22, 1987Date of Patent: January 3, 1989Assignee: Bristol-Myers CompanyInventors: Dolatrai M. Vyas, Paul M. Skonezny
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Patent number: 4792617Abstract: This invention covers a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, Y is lower alkyl or ##STR2## wherein Z is hydrogen, halo, methyl, methoxy or trifluoromethyl; and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta..Type: GrantFiled: February 27, 1987Date of Patent: December 20, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: Gary F. Cooper, John H. Fried, L. David Waterbury
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Patent number: 4786649Abstract: Novel 1-thienyl-4-oxoquinoline-3-carboxylic acid compounds of the formula ##STR1## wherein R.sup.1 is an amino (lower) alkyl, R.sup.2 is thienyl, and X is a halogen atom, and a pharmaceutically acceptable salt thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition comprising as an active ingredient said 1-thienyl-4-oxoquinoline-3-carboxylic acid compounds or a pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable diluent or carrier.Type: GrantFiled: November 13, 1986Date of Patent: November 22, 1988Assignee: Otsuka Pharmaceutical Company LimitedInventors: Hiraki Ueda, Hisashi Miyamoto
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Patent number: 4783213Abstract: Compounds of the formula ##STR1## wherein X is oxy, thio, sulfinyl or sulfonyl;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or phenyl;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.Type: GrantFiled: August 20, 1987Date of Patent: November 8, 1988Assignee: Stauffer Chemical CompanyInventor: David L. Lee
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Patent number: 4781751Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, halogen, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl, with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is halogen, cyano, nitro, trifluoromethyl, --C(O)--OR.sup.f wherein R.sup.f is C.sub.1 -C.sub.4 alkyl, or --C(O)NR.sub.2.sup.b wherein R.sup.b is hydrogen or C.sub.1 -C.sub.2 alkyl;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.Type: GrantFiled: October 2, 1987Date of Patent: November 1, 1988Assignee: Stauffer Chemical CompanyInventor: Hsiao-Ling M. Chin
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Patent number: 4782176Abstract: Phenoxycarboxylic acids of the formula ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4 R.sub.5, Z and n are as hereinafter set forth, are as described. The compounds of formula I are antagonists of slow reacting substance of anaphylaxis (SRS-A), which renders them useful as agents for the treatment of allergic conditions.Type: GrantFiled: May 23, 1983Date of Patent: November 1, 1988Assignee: Hoffmann-La Roche Inc.Inventors: Matthew Carson, Ronald A. LeMahieu, William C. Nason
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Patent number: 4780562Abstract: This invention relates to a process for making a compound of formula I ##STR1## in the form of a stereoisomer or mixture thereof, wherein R is hydrogen, lower alkyl; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta., or a pharmaceutically acceptable, non-toxic salt of the compound wherein R is hydrogen; novel intermediates useful for preparing these compounds; processes for making the intermediates; and a stereoisomer of the compound of formula I wherein R is methyl and X is hydrogen and a process for making same.Type: GrantFiled: September 13, 1985Date of Patent: October 25, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: Gary F. Cooper, Douglas L. Wren, Albert R. Van Horn, Tsung-Tee Li, Colin C. Beard
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Patent number: 4780550Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m -- wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R hu d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)-- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.Type: GrantFiled: September 17, 1987Date of Patent: October 25, 1988Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4777281Abstract: The invention relates to novel [(3,4-dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-substituted-2-phenanthreny l)ox yl]-alkanoic acids and -ethanimidamides 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: March 3, 1986Date of Patent: October 11, 1988Assignee: Merck & Co., Inc.Inventors: Otto W. Woltersdorf, Jr., Edward J. Cragoe, Jr.
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Patent number: 4767879Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, 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.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl;m is an integer chosen from 3 to 5.Type: GrantFiled: December 17, 1986Date of Patent: August 30, 1988Assignee: ICI Australia LimitedInventors: Keith G. Watson, Lynette A. Garson, Graham J. Bird, Lindsay E. Cross, Graeme J. Farquharson
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Patent number: 4766147Abstract: Novel 5-alkylidene-4-substituted-2-cyclopentenones and 5-(1-hydroxy-aliphatic hydrocarbon)-4-substituted-2-cyclopentenones.These novel cyclopentenones and 5-alkylidene-3-hydroxy-4-substituted cyclopentanones have a pharmaceutical activity for treatment of tumors.Type: GrantFiled: January 29, 1986Date of Patent: August 23, 1988Assignee: Teijin LimitedInventors: Ryoji Noyori, Masanori Fukushima, Seizi Kurozumi, Satoshi Sugiura
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Patent number: 4765825Abstract: The invention relates to new aryloxy phenoxy acyl malonates of the general Formula I ##STR1## a process for the preparation thereof and herbicidal compositions comprising the same.In the general Formula IR.sup.1 stands for hydrogen, halogen, trifluoromethyl, trifluoromethoxy or cyano;R.sup.2 represents hydrogen, halogen or methyl;R.sup.3 is C.sub.1-4 alkyl; and the R.sup.3 substituents may be the same or different,X stands for --N.dbd. or --CH.dbd. andn is 0 or 1.The compounds of the general Formula I may be prepared by reacting a compound of the general Formula II ##STR2## with a metal derivative of a malonate of the general Formula III ##STR3## or in the presence of a metal compound with a malonate of the general Formula III; or reacting a compound of the general Formula IV ##STR4## with a compound of the general Formula V; ##STR5## or reacting a compound of the general Formula VI ##STR6## with a compound of the general Formula VII ##STR7## (in which Formulae R.sup.1, R.sup.2, R.sup.Type: GrantFiled: September 23, 1986Date of Patent: August 23, 1988Assignees: Budapesti Vegyimuvek, MTA Kozponti Kemiai Kutato IntezetInventors: Tamas Komives, Ferenc Dutka, Istvan Barta, Istvan Jablonkai, Agnes Hulesch, Ferenc Bihari, Gyula Eifert, Peter Bohus, Katalin Tromfos, Agnes Meszaros nee Szekrenyesi, Istvan Kuronya
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Patent number: 4762844Abstract: Alkyl-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids of the formula ##STR1## in which X.sup.1, X.sup.2 and X.sup.3 each independently is hydrogen, a nitro group, a halogen atom or an alkyl radical with 1 to 3 carbon atoms, with the proviso that at least one of them is an alkyl radical,or pharmaceutically acceptable salts or hydrates thereof, are antibacterially active and promote animal growth.Type: GrantFiled: November 5, 1985Date of Patent: August 9, 1988Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Michael Schriewer, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4761503Abstract: This invention relates to pharmaceutical compositions containing a class of 5-phenyl-1,3-dioxoalkenyl compounds useful as inhibitors of leukotriene biosynthesis and thus useful in the treatment of conditions associated with leukotrienes. This invention also relates to the use of the 5-phenyl-1,3-dioxoalkenyl compounds in the inhibition of leukotriene biosynthesis and thus in the treatment of conditions associated with leukotrienes. This invention further relates to a novel process for the preparation of the 5-phenyl-1,3-dioxoalkenyl compounds.Type: GrantFiled: November 7, 1986Date of Patent: August 2, 1988Assignee: G. D. Searle & Co.Inventors: Richard A. Partis, Richard A. Mueller
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Patent number: 4734512Abstract: There are disclosed intermediates which can be converted into podophyllotoxin and related compounds, which are known antineoplastic agents. There are also disclosed processes for the preparation of such intermediates, and processes for the conversion of the intermediates into known intermediates which are readily converted into podophyllotoxin and related compounds.Type: GrantFiled: December 5, 1985Date of Patent: March 29, 1988Assignee: Bristol-Myers CompanyInventors: Takushi Kaneko, Henry S. L. Wong
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Patent number: 4731471Abstract: The invention relates to novel [(5,6-dichloro-3-oxo-2,3,9,9a-tetrahydrofluoren-7-yl)]alkanoic acids and alkanimidamides bearing novel functional 9a-substituents, 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, the neurological problems caused by AIDS, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections, various brain concussions and elevated intracranial pressure.Type: GrantFiled: November 3, 1986Date of Patent: March 15, 1988Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr., Adolph M. Pietruszkiewicz
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Patent number: 4731473Abstract: The present invention is directed to compounds of the general formula I and pharmaceutically acceptable salts thereof: ##STR1## wherein: R=ethyl, propyl or isopropyl; andA=(CH.sub.2).sub.n wherein n is 2, 4 or 5, and C(CH.sub.2).sub.3.Type: GrantFiled: April 4, 1986Date of Patent: March 15, 1988Assignee: Merck & Co., Inc.Inventors: Donald J. Abraham, Otto W. Woltersdorf, Jr., Edward J. Cragoe, Jr.
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Patent number: 4731470Abstract: The invention relates to novel [(5,6-dichloro-3-oxo-2,9a-alkano--2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy] alkanoic acids and alkanimidamides, 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 including that due to AIDS virus, various brain concussions and elevated intracranial pressure.Type: GrantFiled: November 3, 1986Date of Patent: March 15, 1988Assignee: Merck & Co., Inc.Inventors: Adolph M. Pietruszkiewicz, Otto W. Woltersdorf, Jr., Edward J. Cragoe, Jr.
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Patent number: 4728740Abstract: There is provided a novel and efficient stereoselective total synthesis of epipodophyllotoxin and related epipodophyllotoxin compounds of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each are independently hydrogen or (lower)alkoxy, or R.sup.1 and R.sup.2, taken together, is methylenedioxy; R.sup.4 and R.sup.6 each are independently hydrogen or (lower)alkoxy; and R.sup.5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof. The present invention also provides novel intermediates and processes for the preparation of said intermediates, which are then converted into known antineoplastic agents.Type: GrantFiled: September 15, 1986Date of Patent: March 1, 1988Assignee: Bristol-Myers CompanyInventors: Dolatrai M. Vyas, Paul M. Skonezny
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Patent number: 4724263Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m --wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.Type: GrantFiled: June 9, 1986Date of Patent: February 9, 1988Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4719310Abstract: The invention relates to novel ester and amide substituted [2,3-dihydro-4-(3-oxo-1-cyclohexen-1-yl)phenoxy]alkanoic acids 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: December 23, 1985Date of Patent: January 12, 1988Assignee: Merck & Co., Inc.Inventors: Adolph M. Pietruszkiewicz, Otto W. Woltersdorf, Jr., Edward J. Cragoe, Jr.
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Patent number: RE33033Abstract: .Iaddend.hypercholesterolemic compounds of the HMG-CoA reductase type of the following general formula (1): ##STR1## involving an enantioselective aldol condensation is disclosed.Type: GrantFiled: September 18, 1987Date of Patent: August 22, 1989Assignee: Merck & Co., Inc.Inventors: Joseph E. Lynch, Ichiro Shinkai, Ralph P. Volante