Two Ring Sulfurs In The Hetero Ring Patents (Class 549/20)
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Patent number: 5405968Abstract: Methine dyes with a polyketo group I ##STR1## where A is ##STR2## R.sup.1 is a 5- or 6-membered cycloaliphatic radical which contains one or two hetero atoms from the group --NR.sup.4 --, --O-- and --S-- and which may be fused to an isoaromatic or heteroaromatic group, R.sup.2 and R.sup.3 are identical or different C.sub.1 -C.sub.10 -alkyl groups or together one of the radicals R.sup.1, and m and n are identical or different integers from 0 to 3, are useful as drugs, for producing singlet oxygen, as sensitizers in electrophotographic layers and for photopolymerizations and as laser light sensitive dyes in optical recording media; also novel triketo- and tetraketomethine dyes.Type: GrantFiled: September 27, 1993Date of Patent: April 11, 1995Assignee: BASF AktiengesellschaftInventors: Bernhard Albert, Knut Kessel, Hans-Dieter Martin, Stefan Silber
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Patent number: 5296505Abstract: The invention relates to a stereospecific derivative of formula: ##STR1## in which R is hydrogen or a C.sub.1 -C.sub.4 thioalkyl. The invention also relates to the use of these compounds for the manufacture of stereospecific retinal or retinoic acid, as well as to a process for preparing the retinoids of formula (I). The invention finally relates to a cosmetic or pharmaceutcial composition which contains at least one compound of formula (I) in a suitable vehicle; the pharmaceutical composition according to the invention may be used for treating dermatological, rheumatic, respiratory or ophthalmological conditions.Type: GrantFiled: June 12, 1992Date of Patent: March 22, 1994Assignee: L'OrealInventors: Guy Solladie, Valerie Berl, Jean Maignan
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Patent number: 5283355Abstract: Compounds of the Formula (5) and processes for their preparation and use, particularly in the manufacture of unsymmetrical triphenodioxazine dyes: ##STR1## wherein: Y is H, alkyl, substituted alkyl, alkoxy, Cl or Br;R is a group of Formula (3) ##STR2## R.sup.1 and R.sup.2 are each independently alkyl, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form an optionally substituted 4, 5 or 6 membered alicyclic or heterocyclic ring;R.sup.3 is H;Z is Cl, Br or A--NH; andA is H or the residue of a primary amine.Type: GrantFiled: October 22, 1991Date of Patent: February 1, 1994Assignee: Imperial Chemical Industries PLCInventor: William J. E. Norris
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Patent number: 5202348Abstract: This invention pertains to a novel group of Thiarubrine substances and closely related derivatives, useful as antifungal and antibiotic agents.Type: GrantFiled: August 17, 1990Date of Patent: April 13, 1993Assignee: The University of British ColumbiaInventors: G. H. Neil Towers, Reimer C. Bruening, Felipe Balza, Zyta A. Abramowski, Isabel Lopez-Bazzochi
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Patent number: 5086187Abstract: Compounds of the general formula, including isomers and tautomers thereof: ##STR1## wherein: R.sup.1 to R.sup.5 are as defined in the text; the compounds have herbicidal and plant growth regulating properties; including compositions containing them, methods for using them and intermediates for making them.Type: GrantFiled: May 31, 1990Date of Patent: February 4, 1992Assignee: Dunlena Pty. LimitedInventors: Janet E. Anderson-McKay, Andris J. Liepa
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Patent number: 4985411Abstract: The present invention provides compounds of the formula (I): ##STR1## wherein m and n are independently selected from 0, 1 or 2, ##STR2## R is selected from hydrogen, methyl or ethyl; R.sup.1 is selected from C.sub.1-4 hydrocarbyl substituted by one to five halo atoms, and a group --C.tbd.C--R.sup.9 wherein R.sup.9 is a group S(O).sub.w --R.sup.10 wherein R.sup.10 is trifluoromethyl, methyl or ethyl and w is 0, 1 or 2 or R.sup.9 is a C.sub.3-5 aliphatic group or an aliphatic group containing up to 5 carbon atoms atoms substituted by C.sub.1-4 alkoxy, C.sub.2-6 alkoxyalkoxy, C.sub.1-8 acyloxy, halo or hydroxy, a group COR.sup.11 wherein R.sup.11 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or a group NR.sup.12 R.sup.13 wherein R.sup.12 and R.sup.13 are independently selected from hydrogen, methyl or ethyl, or R.sup.9 is SiR.sup.14 R.sup.15 R.sup.16 wherein R.sup.14 to R.sup.16 are the same or different and each is a C.sub.1-4 aliphatic group or R.sup.14 and R.sup.15 are C.sub.1-4 aliphatic groups and R.sup.Type: GrantFiled: November 29, 1989Date of Patent: January 15, 1991Assignees: The Wellcome Foundation Ltd., The Regents of the University of CaliforniaInventors: John E. Casida, Michael Elliott
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Patent number: 4975457Abstract: Certain trans-2,3-disubstituted-2,3-dihydro-5-hydroxybenzofurans are described. The synthesis involves an intramolecular Michael addition to yield the thermodynamic trans isomer. The compounds were found to be inhibitors of 5-lipoxygenase, an enzyme crucial to the biosynthesis of leukotrienes and useful for the treatment of various inflammatory diseases.Type: GrantFiled: September 25, 1989Date of Patent: December 4, 1990Assignee: Merck & Co., Inc.Inventors: Kathleen M. Rupprecht, Joshua S. Boger
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Patent number: 4946861Abstract: The invention relates to the use of ketenethioacetals of the formula ##STR1## in which R.sub.1 represents aryl or heteroaryl, R.sub.2 represents hydrogen, an optionally substituted hydrocarbon radical, heteroaryl, an acyl radical, a group of the formula --S(O).sub.m --R.sub.a, wherein m is 0, 1 or 2 and R.sub.a is an optionally substituted hydrocarbon radical; or optionally functionally modified sulpho, A represents an optionally substituted bivalent aliphatic hydrocarbon radical and n is 0 or 1, and pharmaceutically acceptable salts of such compounds that contains a salt-forming group, for the treatment of liver diseases, respiratory tract diseases and vascular diseases pharmaceutical preparations containing compounds of the formula I and novel compounds of the formula I. The compounds have liver-protecting and immunomodulating properties.Type: GrantFiled: November 14, 1988Date of Patent: August 7, 1990Assignee: Zyma SAInventors: Andre J. Weith, Philippe M. Narld
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Patent number: 4927845Abstract: Anthralin analogues containing a thio-substituent, especially in one or more of the positions 2-, 7- and 10- of the anthralin ring. They may be made by reacting an anthralin derivative (e.g. 10-bromoanthralin) with a thiol or a compound containing a group convertible to a thio-group. Alternatively, a 1,8-dihydroxy anthraquinone containing a thio-substituent may be reduced. Reactive intermediates may be made by introducing one or more nuclear allylic groups into a 1,8-dihydroxy anthraquinone and then converting them into a reactive form, e.g. by epoxidation or halide addition. The intermediate can then reduced to the oxidation state corresponding to anthralin.Additional products having the 10-carbon atom of the anthralin ring as part of a heterocyclic ring, may be made by anthralins containing various substitutes thioalkyl groups as the 10-substituent.The compounds are useful for treatment of psoriasis, and may be formulated in the conventional vehicles for topical application, for example petrolatum.Type: GrantFiled: August 15, 1989Date of Patent: May 22, 1990Assignee: The Victoria University of ManchesterInventor: John M. Bruce
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Patent number: 4898986Abstract: Disclosed is a novel inosose compound represented by the general formula: ##STR1## wherein X.sup.1 and X.sup.2 are both halogen; X.sup.1 is hydrogen and X.sup.2 is halogen; or X.sup.1 is --SQ.sup.1 and X.sup.2 is --SQ.sup.2 (each of Q.sup.1 and Q.sup.2 is lower alkyl or Q.sup.1 and Q.sup.2 may form lower alkylene), R.sup.1 is a protective group for hydroxyl and Y is .dbd.O, .dbd.N--Z (Z is hydroxyl which may be protected) or ##STR2## (A is hydrogen or an amine residue), particularly to the compound wherein the symbol Y is oxygen.The inosose compound is useful as intermediates for production of valiolamine and the N-substituted derivatives thereof, which have potent .alpha.-glucosidase inhibiting activities and are useful as preventives or therapeutics for symptoms of hyperglycemia and various diseases derived therefrom in human and animals, such as diabetes, obesity and hyperlipemia.Type: GrantFiled: August 31, 1987Date of Patent: February 6, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Satoshi Horii, Hiroshi Fukase
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Patent number: 4889939Abstract: Compounds suitable for being used as lubricants, having general formula:(I) RO--(C.sub.3 F.sub.6 O).sub.m --(CFXO).sub.n --CFX--L, or(II) R"CFXO--(C.sub.3 F.sub.6 O).sub.x (CFXO).sub.y --(C.sub.2 F.sub.4 O).sub.z --CFX--L, whereR=--CF.sub.3, --C.sub.2 F.sub.5, --C.sub.3 F.sub.7X=F, --CF.sub.3R"=F, --CF.sub.3, --C.sub.2 F.sub.5m=an integer from 3 to 100n=a finite integer, or =zero, wherefore m+n ranges from 3 to 100, provided that, if n is finite, m/n ranges from 5 to 20 and R is preferably =CF.sub.3, if n=zero, R is preferably --C.sub.2 F.sub.5 or --C.sub.3 F.sub.7x=a finite integer, or =zeroy, z=finite integers, such that x+y+z ranges from 5 to 200, while (x+z)/y ranges from 5 to 0.5, provided that when x=zero, z/y ranges from 1 to 0.5 and y+z ranges from 5 to 200 n while X is preferably F, and R"=LL=group Y-Z, where:Y=--CH.sub.2 O--, --CH.sub.2 --OCH.sub.2, --CF.sub.2, --CF.sub.Type: GrantFiled: April 11, 1988Date of Patent: December 26, 1989Assignee: Montedison S.p.A.Inventors: Gerardo Caporiccio, Ezio Strepparola, Mario A. Scarati
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Patent number: 4853151Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.Type: GrantFiled: August 11, 1987Date of Patent: August 1, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankfter HaftungInventors: Fritz Vogtle, Wolfgang Calaminus
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Patent number: 4846998Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.Type: GrantFiled: November 21, 1986Date of Patent: July 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
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Patent number: 4822813Abstract: Novel 3-(2-haloalkyl)-1,4-oxathiins or 2-(2-haloalkyl)-1,4-dithiins, useful for regressing or inhibiting the growth of leukemia and tumors in mammals. The compounds have the formula.: ##STR1## wherein R.sub.1 is an alkyl group containing up to 4 carbon atoms, cyclohexyl or phenyl;R.sub.2 is hydrogen or ethyl;R.sub.3 and R.sub.4 are each hydrogen, methyl or ethyl, andwhen either R.sub.3 and R.sub.4 is methyl or ethyl, the other is hydrogen;X is halogen; andY is oxygen or sulfur andwhen Y is sulfur, R.sub.3 and R.sub.4 are both hydrogen.and pharmaceutical compositions comprising said compounds in admixture with a pharmaceutically acceptable substantially non-toxic carrier.Type: GrantFiled: January 21, 1988Date of Patent: April 18, 1989Assignee: Uniroyal Chemical Ltd./Uniroyal Chemical LteeInventors: Walter G. Brouwer, Ethel E. Felauer, Marshal Kulka
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Cyclohexenone derivatives, the preparation and use thereof as herbicides and plant growth regulators
Patent number: 4761486Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, A and X have the meanings given in the disclosure, a process for their manufacture, herbicidal and plant growth-regulating agents containing the novel active ingredients, and methods of combating unwanted plant growth and of regulating plant growth.Type: GrantFiled: January 14, 1987Date of Patent: August 2, 1988Assignee: BASF Aktiengesellschaft, PatentabteilungInventors: Bernd Zeeh, Dieter Jahn, Michael Keil, Dieter Kolassa, Bruno Wuerzer, Norbert Meyer, Wilhelm Rademacher, Johann Jung -
Patent number: 4726911Abstract: Compounds of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or CO groups and/or --OCO-- groups and/or --COO-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, --A.sup.4 --A-- or --A--A.sup.4 --,A is a 1,3-dioxane-2,5-diyl or 1,3-dithiane-2,5-diyl group which is monosubstituted or polysubstituted in the 2-position and/or 4-position by alkyl each having 1-10 C atoms and/or in the 5-position by alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy each having 1-5 C atoms, or by F, Cl, Br or CN,A.sup.2, A.sup.3 and A.sup.4 each are 1,3-dithiane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2,2,2]octylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,4-phenylene, 1,4-phenylene which is substituted by one or two F and/or Cl atoms and/or CH.sub.Type: GrantFiled: October 17, 1985Date of Patent: February 23, 1988Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Joachim Krause, Peter Fuss, Reinhard Hittich, Bernhard Scheuble
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Patent number: 4704227Abstract: Compounds of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H, an alkyl, alkoxy, alkanoyl, alkanoyloxy or alkoxycarbonyl group with in each case 1-10 C atoms, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, --A.sup.4 --A--or --A--A.sup.4 --,A is a 1,3-dioxane-2,5-diyl or a 1,3-dithiane-2,5-diyl group,A.sup.2, A.sup.3 are each a 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl,and A.sup.4 1,3-dithiane-2,5-diyl, piperidine-1,4-diyl or 1,4-bicyclo(2,2,2)octylene group, or a 1,4-phenylene, pyrimidine-2,5-diyl or pyridazine-3,6-diyl group which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups and/or CN groups,Z.sup.1 and Z.sup.2 are each --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O or a single bond andR.sup.3 is H, an alkyl, alkoxy, alkanoyl, alkanoyloxy or alkoxycarbonyl group with in each case 1-10 C atoms, F, Cl, Br or CN, with the proviso that(a) at least one group A.sup.2, A.sup.Type: GrantFiled: February 15, 1985Date of Patent: November 3, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Krause, Andreas Wachtler, Reinhard Hittich, Georg Weber, Bernhard Scheuble
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Patent number: 4639328Abstract: Thienothiophene derivatives of the formula IR.sup.1 --(A.sup.1).sub.m --Z.sup.1 --A--(Z.sup.2 --A.sup.2).sub.n --R.sup.2 Iin which R.sup.1 and R.sup.2 are each H or an alkyl group having 1-12 C atoms, in which, furthermore, one or two non-adjacent CH.sub.2 groups can be replaced by O atoms, --CO-- or --CH.dbd.CH-- groups, or are each F, Cl, Br, CN, --COOR or --O--COR, A.sup.1 and A.sup.2 are each 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl, tetrahydropyran-2,5-diyl, pyridazine-3,6-diyl or the corresponding N-oxide, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl groups which are unsubstituted or substituted by one or two F, Cl or Br atoms and/or CN groups and/or CH.sub.3 groups, A is a group of the formula 1 or 2 ##STR1## which is unsubstituted or substituted by one or two Cl and/or Br atoms, Z.sup.1 and Z.sup.2 are each --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.Type: GrantFiled: November 26, 1984Date of Patent: January 27, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Krause, Michael Romer, Georg Weber
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Patent number: 4496721Abstract: Symmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.Type: GrantFiled: February 7, 1983Date of Patent: January 29, 1985Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
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Patent number: 4464538Abstract: Disclosed is a method for synthesizing dihydro-1,4-dithiins by the reaction of an acyloin or a halocarbonyl compound with an organic thiosulfate.Type: GrantFiled: May 3, 1983Date of Patent: August 7, 1984Assignee: Uniroyal Ltd.Inventor: Arthur D. Brewer
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Patent number: 4319033Abstract: A method of making certain 2,3-dihydro-1,4-dithiins of the following formula by the action of alpha-hydroxyketones (acyloins) of 1,2-dithiols: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen or alkyl having 1 to 6 carbon atoms or are joined together to form a ring with 3 or 4 methylene groups, and R.sup.3 and R.sup.4 are hydrogen or the same or different alkyl groups having 1 to 10 carbon atoms, which alkyl groups may be substituted with lower alkoxy groups.Type: GrantFiled: March 26, 1981Date of Patent: March 9, 1982Assignee: Uniroyal Ltd.Inventors: Allan K. S. Tsai, Duncan D. Lennox, Arthur D. Brewer
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Patent number: 4273785Abstract: Novel 4-monoalkylamino-benzaldehydes, 4-mono-alkylamino-alkanophenones, and 4-monoalkylamino-benzophenones, and derivatives and salts thereof, are disclosed which are useful as anti-atherosclerotic agents.Type: GrantFiled: September 27, 1977Date of Patent: June 16, 1981Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4265807Abstract: Disclosed is a method of disproportionating rosin comprising heating said rosin in the presence of a dithiin derivative such, for example, as 2,5-diphenyl dithiin. The method can be carried out at about 150.degree. C. to about 300.degree. C. for about 1 hour to about 10 hours with the longer reaction time corresponding to the lower temperatures. Preferably, the process is run at about 260.degree. C. to about 300.degree. C. for about 3 to 8 hours.Type: GrantFiled: January 22, 1980Date of Patent: May 5, 1981Assignee: Hercules IncorporatedInventor: David S. Breslow
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Patent number: 4259507Abstract: 3,5-di-(2-methylpropyl)-1,2,4-trithiolane having the formula: ##STR1## and its "cis" and "trans" isomers represented by the structures: ##STR2## and described as being useful in augmenting or enhancing the organoleptic properties (taste and aroma) of foodstuffs.Type: GrantFiled: August 3, 1979Date of Patent: March 31, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Chi-Kuen Shu, Braja D. Mookherjee, Manfred H. Vock
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Patent number: 4255182Abstract: Disclosed are compounds of the formula ##STR1## wherein R.sup.1 is alkyl, R.sup.2 is selected from the group consisting of hydrogen and alkyl; or R.sup.1 and R.sup.2 together with the nitrogen atom form a cyclic ring structure having 4 or 5 carbon atoms; m is the integer 0 or 1; when m is 1, R.sup.4 and R.sup.5 are each independently selected from the group consisting of hydrogen and alkyl or up to 3 carbon atoms; when m is 0, R.sup.4 is hydrogen and R.sup.5 is the same as defined above; R.sup.3, R.sup.6, R.sup.7, R.sup.8, R.sup.9 are each independently selected from the group consisting of hydrogen and alkyl; n is an integer from 0 to 2; and Z.sup.1 and Z.sup.2 are each independently selected from the group consisting of oxygen and sulfur. These compounds are useful as herbicides.Type: GrantFiled: March 10, 1980Date of Patent: March 10, 1981Assignee: Velsicol Chemical CorporationInventor: John Krenzer