Chalcogen Attached Indirectly To The Five-membered Hetero Ring By Acyclic Nonionic Bonding Patents (Class 548/562)
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Patent number: 4891432Abstract: Novel phenoxy derivatives are provided which can be represented by the general formula: ##STR1## wherein the various substituents are as defined, and include compounds such as benzyl 6-[p-[5-(1-imidazolyl)pentyloxy]phenoxy]-2,2-dimethylhexanoate.The invention also encompasses pharmaceutical compositions containing the derivatives and their use in treating tumors.Type: GrantFiled: July 16, 1987Date of Patent: January 2, 1990Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Noriki Ito, Yoshinobu Nagano, Akihiro Tanaka, Yoso Numasaki, Koichiro Takahashi
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Patent number: 4874871Abstract: 2,3-Dihydro-1H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid compounds of the formula, ##STR1## in which Y is OH;O.sup.- M.sup.+, wherein M is an alkali metal; orNRR', wherein R is lower alkyl and R' is lower alkyl or aryl, or NRR' is the residue of a saturated cyclic amine,are prepared from pyrrole.Type: GrantFiled: March 25, 1987Date of Patent: October 17, 1989Assignee: Syntex (U.S.A.) Inc.Inventors: Michael P. Fleming, George C. Schloemer, Hiralal N. Khatri
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Patent number: 4851427Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1-6 alkyl not containing an asymmetric carbon atom, C.sub.3-7 cycloalkyl or ##STR2## wherein R.sub.5, R.sub.6 and R.sub.7 are as defined below, R.sub.2 is C.sub.1-6 alkyl not containing an asymmetric carbon atom, C.sub.3-7 cycloalkyl or ##STR3## wherein R.sub.8, R.sub.9 and R.sub.10 are as defined below. R.sub.3 is hydrogen, C.sub.1-6 alkyl not containing an asymmetric carbon atom, C.sub.3-7 cycloalkyl or ##STR4## wherein R.sub.11, R.sub.12 and R.sub.13 are as defined below, R.sub.4 is hydrogen, C.sub.1-6 alkyl not containing an asymmetric carbon atom, C.sub.7-7 cycloalkyl or ##STR5## wherein R.sub.14, R.sub.15 and R.sub.16 are as defined below, X is --(CH.sub.2).sub.m --, --CH.dbd.CH--, --CH.dbd.CH--CH.sub.2 -- or --CH.sub.2 --CH.dbd.CH--, wherein m is 0, 1, 2 or 3, andZ is ##STR6## wherein R.sub.17 is hydrogen or C.sub.1-3 alkyl, and R.sub.18 is hydrogen, R.sub.19 or M, wherein R.sub.Type: GrantFiled: October 15, 1986Date of Patent: July 25, 1989Assignee: Sandoz Pharm. Corp.Inventor: James R. Wareing
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Patent number: 4841078Abstract: Bicyclic fused benzenoid compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, where M is O, CH.sub.2 or NR.sub.6 ; R.sub.6 is hydrogen, formyl, carbobenzyloxy or certain carboalkoxyalkyl, alkanoyl, alkyl, aralkyl or aralkylcarbonyl groups;A' is:(1) A where one of A and B is hydrogen such that when A is hydrogen, B is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 1 or 2; when B is hydrogen, A is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 0 or 1, when taken together A and OR.sub.1 form a lactone or certain derivatives thereof;(2) A' is ##STR2## (3) A' is Q.sub.3 ; Q is CO.sub.2 R.sub.7, COR.sub.8, C(OH)R.sub.8 R.sub.9, CN, CONR.sub.12 R.sub.13, CH.sub.2 NR.sub.12 R.sub.13, CH.sub.2 NHCOR.sub.14, CH.sub.2 NHSO.sub.2 R.sub.17 or 5-tetrazoyl;Q.sub.3 is ##STR3## 5-tetrazolyl, CH.sub.2 CONHCOR.sub.7, COOH or certain ester, amide, carboximido or sulfonimido derivatives thereof, CONHOH, CONHCONH.sub.2, or COCH.sub.2 Q.sub.4 where Q.sub.Type: GrantFiled: August 9, 1984Date of Patent: June 20, 1989Assignee: Pfizer Inc.Inventors: James F. Eggler, Michael R. Johnson, Lawrence Sherman
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Patent number: 4837327Abstract: Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.Type: GrantFiled: July 13, 1987Date of Patent: June 6, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4829074Abstract: Compounds of the formula: ##STR1## The compounds are useful as pesticides, particularly insecticides.Type: GrantFiled: February 24, 1986Date of Patent: May 9, 1989Assignee: Imperial Chemical Industries PLCInventor: Michael J. Bushell
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Patent number: 4810716Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migraines, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.Type: GrantFiled: March 3, 1987Date of Patent: March 7, 1989Assignee: Warner-Lambert CompanyInventors: David T. Connor, Daniel L. Flynn
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Patent number: 4798894Abstract: Compounds containing at least one N,N-dialkylatable amino or amido group (e.g., aniline, dodecylamine, acetamide) are converted in a highly efficient manner into gem cyclodialkylated compounds by reaction with an unstrained cyclic ether (e.g., tetrahydrofuran) or a polyol (e.g., 1,4-butane diol) cyclizable to an unstrained ether using titanium dioxide catalysts that have prior to use:(1) a surface area of at least 70 square meters per gram (as determined by the BET method), and(2) the capability of chemically adsorbing at 100.degree. C. at least 35.times.10.sup.4 millimoles of gaseous ammonia per square meter of surface area.Type: GrantFiled: May 11, 1987Date of Patent: January 17, 1989Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4798901Abstract: Novel pyrrole derivatives of the formula ##STR1## wherein one of R.sub.2 and R.sub.3 is ##STR2## and the other of R.sub.2 and R.sub.3 as well as R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CN, --CF.sub.3, --NO.sub.2, --COOAlk and Alk is alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, ##STR3## n is 0, 1 or 2, R', R.sub.1 ' and R.sub.2 ' are alkyl of 1 to 8 carbon atoms and R.sub.4 and R.sub.5 taken together with the carbon atoms to which they are attached may form an optionally further unsaturated carbon homocycle of up to 8 carbon atoms, Z is selected from the group consisting of hydrogen, --CN, --C.tbd.CH, --CF.sub.3 and alkyl of 1 to 3 carbon atoms, A is the residue of a pyrethrinoid acid, R.sub.Type: GrantFiled: December 2, 1987Date of Patent: January 17, 1989Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute, Laurent Taliani
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Patent number: 4792568Abstract: This invention relates to new lipoxygenase inhibitors possessing anti-inflammatory and anti-allergic properties. The present new compounds are of the formula: ##STR1## and salts thereof; wherein, R is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower aralkyl, phenyl, naphthyl, or a nitrogen oxygen or sulfur heterocyclic; andY.sub.1 and Y are independently hydrogen, lower alkyl, hydroxy, lower alkoxy, aryloxy, lower aralkoxy, aryl, lower aralkyl, carboxy, lower carbalkoxy, lower carbaralkoxy, carbaryloxy, formyl, or alkyl, alkenyl or alkynyl containing up to 6 carbon atoms in the principal chain and up to a total of 10 carbon atoms;provided that when Y and Y.sub.1 are both hydrogen or when Y.sub.1 is hydrogen and Y is CHO, the R is other than hydrogen, unsubstituted phenyl, or lower alkyl.Type: GrantFiled: April 14, 1986Date of Patent: December 20, 1988Assignee: Rorer Pharmaceutical CorporationInventor: Joseph Auerbach
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Patent number: 4748174Abstract: The water soluble acid addition salts of an NSAID, such as acetylsalicylic acid, fenbufen, diflunisal, piroxicam, naproxen, or the like, with either glucamine or meglumine (N-methylglucamine) are useful anti-inflammatory and analgesic drugs, well adopted for parenteral, oral, rectal or topical administration.Type: GrantFiled: January 5, 1987Date of Patent: May 31, 1988Assignee: Therapicon s.r.l.Inventor: Paolo A. Veronesi
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Patent number: 4737513Abstract: Novel pyrrole derivatives of the formula ##STR1## wherein one of R.sub.2 and R.sub.3 is ##STR2## and the other of R.sub.2 and R.sub.3 as well as R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CN, --CF.sub.3, --NO.sub.2, --COOAlk and Alk is alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, ##STR3## n is 0, 1 or 2, R', R.sub.1 ' and R.sub.2 ' are alkyl of 1 to 8 carbon atoms and R.sub.4 and R.sub.5 taken together with the carbon atoms to which they are attached may form an optionally further unsaturated carbon homocycle of up to 8 carbon atoms, Z is selected from the group consisting of hydrogen, --CN, --C.tbd.CH, --CF.sub.3 and alkyl of 1 to 3 carbon atoms, A is the residue of a pyrethrinoid acid, R.sub.Type: GrantFiled: August 13, 1985Date of Patent: April 12, 1988Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute, Laurent Taliani
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Patent number: 4732901Abstract: Compounds of formula (I): ##STR1## in which R.sub.1 is hydrogen or C.sub.1-6 alkyl;R.sub.2 is hydrogen or a group --CO.sub.2 R.sub.3 where R.sub.3 is hydrogen or C.sub.1-6 alkyl;n is an integer of from 2 to 12;X represents a double or triple bond, and each of A and B represents hydrogen when X is a double bond, or both A and B are absent when X is a triple bond; and ##STR2## represents an aromatic heterocyclic ring, are disclosed as inhibitors of 5-lipoxygenase.Type: GrantFiled: February 27, 1986Date of Patent: March 22, 1988Assignee: Beecham Group p.l.c.Inventor: Derek R. Buckle
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Patent number: 4708963Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, a heterocyclic residue, or NHR.sub.3, wherein R.sub.3 is an acid residue or hydrogen;X is oxygen;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D is a straight-chain or branched, saturated or unsaturated aliphatic group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms, 1,2-methylene, 1,1-trimethylene;E is --C.tbd.C-- or --CR.sub.6 .dbd.CH.sub.7 -- wherein R.sub.6 and R.sub.7 are hydrogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group;R.sub.5 is free or functionally modified hydroxy and,when R.sub.Type: GrantFiled: May 28, 1985Date of Patent: November 24, 1987Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
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Patent number: 4705801Abstract: There is described a process for producing fungicidally active 4-phenylpyrrole derivatives of the formula I ##STR1## wherein R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl, and n is 0, 1 or 2, which process comprises reacting a 3-trifluoromethyl-4-phenylpyrrole of the formula II ##STR2## wherein R.sub.n is as defined under the formula I, and R.sub.1 is hydrogen or an acyl group, at elevated temperature and elevated pressure, with ammonia. Important intermediates and the production thereof are also described.Type: GrantFiled: October 7, 1985Date of Patent: November 10, 1987Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Robert W. Lang
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Patent number: 4694018Abstract: The compounds of the present invention comprise substituted 1,5-diphenyl-2-pyrrolepropionic acids and derivatives thereof represented by the formula: ##STR1## wherein: R represents hydroxy, alkoxy of from 1 to 6 carbon atoms, inclusive, or amino; R.sup.1 represents hydrogen or acyl of from 2 to 7 carbon atoms, inclusive; and X represents hydrogen, halogen, hydroxy or alkoxy of from 1 to 6 carbon atoms, inclusive. The compounds of the present invention are 5-lipoxygenase inhibitors and, therefore, are useful in the treatment of local and systemic inflammation, allergy and hypersensitivity reactions and other disorders in which agents formed in the 5-lipoxygenase metabolic pathway are involved.Type: GrantFiled: November 29, 1985Date of Patent: September 15, 1987Assignee: G. D. Serale & Co.Inventor: Leland J. Chinn
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Patent number: 4692464Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is (a) hydrogen, (b) C.sub.1-10 alkyl, (c) C.sub.1-10 alkyl substituted by halogen; C.sub.1-4 alkoxy; C.sub.6-10 aryl; C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group; di-C.sub.1-4 -alkylamino; or tri-C.sub.1-4 -alkylammonium, (d) C.sub.4-10 cycloalkyl, (e) C.sub.4-10 cycloalkyl substituted by C.sub.1-4 alkyl, (f) C.sub.6-10 aryl, (g) C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group, or (h) an aromatic heterocycle of 5 or 6 ring atoms one of which is O, N or S;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--;W is hydroxymethylene, RO-methylene, CH.sub.3 or CH.sub.3, ##STR2## wherein OH or OR is in the .alpha.- or .beta.Type: GrantFiled: February 26, 1982Date of Patent: September 8, 1987Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Gerda Mannesmann, Wolfgang Losert, Jorge Casals
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Patent number: 4689342Abstract: Novel esters in all possible isomeric forms or a mixture thereof having the formula ##STR1## wherein Y is selected from the group consisting of hydrogen, halogen, --OAlK and ##STR2## AlK is alkyl of 1 to 6 carbon atoms, n is 0, 1 or 2, Z is selected from the group consisting of --O-- and --S--, R.sub.1 is selected from the group consisting of (a) optionally unsaturated alkyl of 1 to 8 carbon atoms and optionally unsaturated cycloalkyl or cycloalkylalkyl of 3 to 8 carbon atoms optionally substituted with at least one member of the group consisting of halogen, --OH, --SH, --OR', --SR', ##STR3## --SO.sub.2 AlK.sub.2, --SO.sub.3 AlK.sub.3, aryl optionally substtuted with at least one member of the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --CF.sub.3, --OCF.sub.3, --SCF.sub.3 and ##STR4## R' is alkyl of 1 to 8 carbon atoms, R" and R'" are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, AlK.sub.1, AlK.sub.2 and AlK.Type: GrantFiled: November 21, 1983Date of Patent: August 25, 1987Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute
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Patent number: 4675419Abstract: The invention relates to a process for preparing .alpha.-hydroxy-acids of general formula: ##STR1## in which R represents hydrogen or a lower alkyl radical and Cy represents a phenyl, naphthyl or heterocyclic radical, these latter three radicals optionally comprising one or more substituents selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy radicals and halogen atoms, process which comprises the treatment of an .alpha.-monohalogenated ketone of general formula: ##STR2## in which R and Cy have the same meaning as above and X represents chlorine, bromine or iodine, in the presence of an aqueous solution of an alkali metal hydroxide, a non-polar organic solvent selected from an aromatic or alicyclic hydrocarbon and oxygen in excess optionally in the presence of an inert gas, the treatment being carried out at a temperature ranging from the boiling temperature of the reaction medium at atmospheric pressure and 240.degree. C.Type: GrantFiled: November 21, 1985Date of Patent: June 23, 1987Assignee: SanofiInventors: Jean-Daniel Andre, Pierre-Jean Grossi, Alain Heymes, Giovanni V. Manzaroli
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Patent number: 4654431Abstract: A novel photocurable monomer having the formula: ##STR1## wherein: Ar is arylene;R.sup.1 is H, alkyl, alkoxy, amino, halogen, sulfide, sulfoxide, sulfonate, aryl or heterocyclic;R.sup.2 is H, alkyl, aryl or aralkyl; andR.sup.3 is H or methyl,is useful in preparing a polymer having a high refractive index. The polymer is useful in optical components, such as lenses.Type: GrantFiled: September 10, 1982Date of Patent: March 31, 1987Assignee: Eastman Kodak CompanyInventor: Charles D. DeBoer
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Patent number: 4647576Abstract: 6-[2-(Substituted-pyrrol-1-yl)alkyl]pyran-2-ones and the corresponding ring-opened hydroxy-acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutarylcoenzyme A reductase (HMG-CoA reductase), and are thus useful hypolipidemic and hypocholesterolemic agents. Pharmaceutical compositions containing such compounds, and a method of treatment employing such pharmaceutical compositions are also disclosed.Type: GrantFiled: December 10, 1984Date of Patent: March 3, 1987Assignee: Warner-Lambert CompanyInventors: Milton L. Hoefle, Bruce D. Roth, Charlotte D. Stratton
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Patent number: 4644009Abstract: Provided are new compounds having valuable therapeutic activity. These compounds are of the formula: ##STR1## and salts thereof, whereinX=O, S or NR.sub.2 ;Z=(CHR.sub.3).sub.n C(R.sub.3))OH)--, ##STR2## --CH.sub.3 .dbd.CH.sub.3 CR.sub.3 (OH)--, or --(CHR.sub.3).sub.n', M=--O--, --S--, or ##STR3## Z.sub.1 is an alkylene chain of 0-5 carbon atoms in the principal chain and a total of 7 carbon atoms;R.sub.1 is H, phenyl, naphthyl or a sulfur, nitrogen or oxygen-heterocyclic ring;R.sub.2 is H, alkyl, aryl or aralkyl;R.sub.3 is H or CH.sub.3 ;n=0-5; andn'=1-5.Type: GrantFiled: October 29, 1984Date of Patent: February 17, 1987Assignee: USV Pharmaceutical CorporationInventors: Fu-chih Huang, Joseph Auerbach
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Patent number: 4629798Abstract: Organic polymers which are "hydroxyphenyl-substituted" and "ether-substituted" polypyrroles ("PP") linked through N-adjacent C atoms, are disclosed which are compactable, extrudable and are also electrical conductors. When such PPs are prepared by electrochemical deposition with an appropriate electrolyte, they are also soluble in commonly available solvents, provided at least one of the 3- or 4-positions of the pyrrole nucleus is substituted with a substituent having either a hydroxyphenyl, or an ether structure. By choice of the hydroxyphenyl and/or ether substituent on one of the substitutable positions (3- or 4-) of the pyrrole nucleus, or both, the PP may be tailored for use either as a semiconductor having a conductivity in the range from about 10.sup.-5 to about 10.sup.-2 S/cm, or a relatively good conductor having a conductivity in the range from about 10.sup.-2 to about 10.sup.2 S/cm.Type: GrantFiled: August 19, 1985Date of Patent: December 16, 1986Assignee: The B. F. Goodrich CompanyInventor: Lee Traynor
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Patent number: 4626592Abstract: Amines and amides are N,N-cyclodialkylated by reaction with an unstrained cyclic ether in the presence of a B-subgroup metal oxide alkylation catalyst, preferably a Group IV-B metal oxide such as titanium dioxide.Type: GrantFiled: December 24, 1984Date of Patent: December 2, 1986Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4563477Abstract: A process for the preparation of alpha-(N-pyrrolyl)-derivative acids, the salts and esters thereof, of the formula ##STR1## in which R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen atoms or substituted or unsubstituted alkyl, aryl, alkylaryl or heterocyclic radicals and R' is a metal cation, an organic base or an organic radical, wherein the corresponding amino ester is reacted with a dialkoxytetrahydrofuran or a derivative thereof. Certain compounds comprised among those corresponding to the above formula, particularly the DL, D and L-alpha-(N-pyrrolyl)-phenylacetic acids and certain esters thereof. Therapeutical compositions containing such compounds as active ingredient and therapeutical applications of said compounds.Type: GrantFiled: May 13, 1983Date of Patent: January 7, 1986Assignee: Antibioticos, S.A.Inventors: Francisco S. Maldonado, Luis C. Pla, Jose L. F. Puentes, Jose M. F. Sousa-Faro
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Patent number: 4535166Abstract: Rearrangement of alpha-halo-alkylarylketals in neutral or weakly alkaline conditions and in the presence of a polar-protic medium and subsequent hydrolysis of the thus obtained esters, in the same reaction medium, to afford the corresponding alpha-arylalkanoic acids or their salts which are particularly useful as anti-inflammatory, analgesic and antipyretic agents.Type: GrantFiled: August 3, 1983Date of Patent: August 13, 1985Assignee: Zambon S.p.A.Inventors: Graziano Castaldi, Claudio Giordano
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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: 4529721Abstract: A compound of the formula: ##STR1## wherein u represents hydrogen, carboxamido, N-hydroxycarboxamido, carboxy, azido, an aryl, an acylamino, a protected carboxy or an N-alkoxycarboxamido, or, together with v, can represent --S-- or --CH.sub.2 S--; v represents hydrogen, halogen, cyano or an alkylthio, or, together with u, can represent --S-- or --CH.sub.2 S--, or, together with w, can represent --(CH.sub.2).sub.3 CO--; w represents hydrogen, carboamoyl, cyano, carboxy, an N-alkylcarbamoyl, an alkyl, an aryl, a protected carboxy or a heterocycle, or, together with v, can represents --(CH.sub.2).sub.Type: GrantFiled: September 21, 1983Date of Patent: July 16, 1985Assignee: Shionogi & Co., Ltd.Inventors: Wataru Nagata, Mitsuru Yoshioka, Yasuhiro Nishitani, Tsutomu Aoki, Toshiro Konoike, Tadatoshi Kubota
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Patent number: 4504303Abstract: There are disclosed derivatives of five-membered nitrogen-containing heterocycles substituted on the nitrogen atom in position 1 by polyfunctional alkenyl groups. Said compounds are endowed with phytogrowth-regulating activity and, in higher doses, with herbicidal activity. A process for synthesizing the compounds and their use in agriculture are also disclosed.Type: GrantFiled: March 16, 1983Date of Patent: March 12, 1985Assignee: Montedison S.p.A.Inventors: Mirella Cecere, Franco Gozzo, Ernesto Signorini
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Patent number: 4495196Abstract: 4,5-Diaryl-.alpha.-polyfluoroalkyl-1H-pyrrole-2-methanols, such as 4,5-bis (4-fluorophenyl)-.alpha., .alpha.-bis (trifluoromethyl)-1H-pyrrole-2-methanol, are useful in treatment of inflammation and relieving pain.Type: GrantFiled: August 19, 1981Date of Patent: January 22, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: George A. Boswell, Jr.
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Patent number: 4493935Abstract: A process for the preparation of esters of 1H-pyrrol-2-acetic acids of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and R.sub.2 is selected from the group consisting of alkyl of 1 to 4 carbon atoms and aralkyl of 1 to 4 alkyl carbon atoms comprising reacting a compound of the formula ##STR2## wherein R.sub.3 is selected from the group consisting of --CN and ##STR3## in an aqueous media with a saponification base wherein the saponification base is added gradually to the 1H-pyrrol-2-acetonitrile and/or 1H-pyrrol-2-acetamide to selectively saponify the same to obtain a substantially isomer-free salt of 1H-pyrrol-2-acetic acid, adding alkali metal bicarbonate to the solution to keep the pH of solution at about 10.2 to 10.Type: GrantFiled: February 2, 1984Date of Patent: January 15, 1985Assignee: Rutgerswerke AktiengesellschaftInventors: Winfried Orth, Werner Fickert
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Patent number: 4473394Abstract: This invention relates to pyrrole sulfonamides which are useful as herbicides. Typical of the pyrrole sulfonamides of the instant application in N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,5-dimethyl-1H-p yrrole-3-sulfonamide.Type: GrantFiled: September 27, 1982Date of Patent: September 25, 1984Assignee: E. I. DuPont De Nemours & CompanyInventors: John C. Budzinski, George Levitt
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Patent number: 4468521Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.Type: GrantFiled: February 22, 1982Date of Patent: August 28, 1984Assignee: Kuraray Co., Ltd.Inventors: Mori Fumio, Omura Toshiaki, Nishida Takashi, Itoi Kazuo
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Patent number: 4458090Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.Type: GrantFiled: October 15, 1981Date of Patent: July 3, 1984Assignee: Kuraray Co., Ltd.Inventors: Mori Fumio, Omura Yoshiaki, Nishida Takashi, Itoi Kazuo
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Patent number: 4451658Abstract: Alkyl 1,4-dialkylpyrrole-2-alkanoates are prepared by the selective decarboxylation of a 1,4-dialkyl-3-carboxypyrrole-2-alkanoic acid or an alkyl ester or alkali metal salt thereof under moderate conditions with a mixture of a strong mineral acid, an alkanol, and water. The products are useful for the preparation of anti-inflammatory agents.Type: GrantFiled: December 9, 1982Date of Patent: May 29, 1984Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4423067Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, a heterocyclic residue, or NHR.sub.3, wherein R.sub.3 is an acid residue or hydrogen;X is oxygen;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D is a straight-chain or branched, saturated or unsaturated aliphatic group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms, 1,2-methylene, 1,1-trimethylene;E is --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 are hydrogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group;R.sub.5 is free or functionally modified hydroxy and,when R.sub.Type: GrantFiled: December 21, 1981Date of Patent: December 27, 1983Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
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Patent number: 4419363Abstract: Novel 1-aryloxy-3-amidoamidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. Representative of the compounds disclosed is 1-(o-cyanophenoxy)-3-.beta.-(2-thenamidoacetamido)ethylaminopropan-2-ol.Type: GrantFiled: June 4, 1982Date of Patent: December 6, 1983Assignee: Imperial Chemical Industries PLCInventor: Leslie H. Smith
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Patent number: 4418202Abstract: Novel 2-vinyl(or ethyl)-1-cyanocyclopropane-1-carboxylates and 2-vinyl(or ethyl)-1-arylcyclopropane-1-carboxylates useful as herbicides, pesticides and chemical intermediates are provided. The invention also relates to a method of modifying plant growth by the application of vinyl(or ethyl)cyclopropane derivatives wherein the carboxylate group contains an amine or quaternized amine moiety.Type: GrantFiled: December 21, 1981Date of Patent: November 29, 1983Assignee: Emery Industries, Inc.Inventors: Richard G. Fayter, Jr., Allen L. Hall
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Patent number: 4408057Abstract: Disclosed are novel compounds of the formula ##STR1## wherein R.sup.1 is a heterocyclic radical selected from furanyl, thienyl, pyridyl, pyrimidyl, oxazolyl, pyrrolyl, isoxazolyl, thiazolyl, and isothiazolyl, and R.sup.2 is hydrogen, a tetramethylcyclopropanecarbonyl group, a 1-(substituted-phenyl)-2-methylpropyl-1-carbonyl group, a 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropanecarbonyl group, or a substituted-vinylcyclopropanecarbonyl group. The compounds wherein R.sup.2 is other than hydrogen are insecticides.Type: GrantFiled: December 20, 1982Date of Patent: October 4, 1983Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4408043Abstract: Fluorinated compounds of the formula ##STR1## are disclosed. The cationic amine compounds are useful as surfactants.Type: GrantFiled: March 8, 1982Date of Patent: October 4, 1983Assignee: Nalco Chemical CompanyInventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
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Patent number: 4404377Abstract: Heterocyclic/aromatic fluorinated compounds of the formula ##STR1## are disclosed. The cationic compounds are useful as surfactants.Type: GrantFiled: March 8, 1982Date of Patent: September 13, 1983Assignee: Nalco Chemical CompanyInventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
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Patent number: 4380656Abstract: Novel 2-vinyl- and 2-ethylcyclopropane carboxylates useful as pesticides, herbicides and chemical intermediates are provided. The products of this invention contain two gem carboxylate ##STR1## groups, which can be the same or different. The carboxylate groups will contain an aliphatic, cycloaliphatic, aromatic, heteroalkyl or heterocyclic moiety.Type: GrantFiled: July 27, 1981Date of Patent: April 19, 1983Assignee: Emery Industries, Inc.Inventor: Richard G. Fayter, Jr.
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Patent number: 4368205Abstract: Disclosed are novel compounds of the formula ##STR1## wherein R.sup.1 is a heterocyclic radical selected from furanyl, thienyl, pyridyl, pyrimidyl, oxazolyl, pyrrolyl, isoxazolyl, thiazolyl, and isothiazolyl, and R.sup.2 is hydrogen, a tetramethylcylopropanecarbonyl group, a 1-(substituted-phenyl)-2-methylpropyl-1-carbonyl group, a 1-(4-ethoxyphenyl)-2-dichlorocyclopropanecarbonyl group, or a substituted-vinyl-cyclopropanecarbonyl group. The compounds wherein R.sup.2 is other than hydrogen are insecticides.Type: GrantFiled: September 17, 1981Date of Patent: January 11, 1983Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4359422Abstract: In a process of preparing 2,2,2-trichloro-1-(N-hydrocarbylpyrryl-2)-ethanol by mixing and reacting essentially equimolar quantities of chloral and N-hydrocarbylpyrrole in a liquid reaction system containing a protonic acid added in the form of an organic acid, improvements have been made. The improvement involves (i) performing the reaction in a methylene chloride reaction medium containing protonic acid added in the form of a carboxylic acid whose acidic dissociation constant is not substantially greater than that of acetic acid, and (ii) proportioning the relative amounts of the chloral, N-hydrocarbylpyrrole and methylene chloride reaction medium so as to result in the formation of a solution of 2,2,2-trichloro-1-(N-hydrocarbylpyrryl-2)-ethanol in the reaction medium having a concentration in the range of about 1 to about 8 molar.Type: GrantFiled: February 1, 1980Date of Patent: November 16, 1982Assignee: Ethyl CorporationInventor: Michael J. Dagani
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Patent number: 4336194Abstract: Carboxylic acid esters of the formula (I), ##STR1## wherein X is a hydrogen atom, or a C.sub.1 -C.sub.3 alkyl or a C.sub.1 -C.sub.3 alkoxyl group or a halogen atom linked to the meta or para position and R.sub.1 is a group of the formula (II) or (III), ##STR2## wherein R.sub.2 is a hydrogen atom or a methyl group, and when R.sub.2 is a methyl group R.sub.3 is also a methyl group, and when R.sub.2 is a hydrogen atom R.sub.3 is a group of the formula, ##STR3## (wherein R.sub.5 is a halogen atom or a C.sub.1 -C.sub.3 alkyl, vinyl or a C.sub.1 -C.sub.3 alkoxymethyl group, R.sub.6 is a hydrogen or halogen atom or a methyl group, or, taken together, R.sub.5 and R.sub.6 may form a tetramethylene group by connecting together at ends thereof), R.sub.4 is a halogen atom or a C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxyl or 3,4-methylenedioxy group, n is 1 or 2 and Y is a isopropyl or cyclopropyl group.Type: GrantFiled: July 13, 1979Date of Patent: June 22, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Tadashi Ohsumi, Nobushige Itaya, Masachika Hirano
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Patent number: RE32896Abstract: Amines and amides are N,N-cyclodialkylated by reaction with an unstrained cyclic ether in the presence of a B-subgroup metal oxide alkylation catalyst, preferably a Group IV-B metal oxide such as titanium dioxide.Type: GrantFiled: March 23, 1987Date of Patent: March 28, 1989Assignee: Ethyl CorporationInventor: Duane C. Hargis