Two Double Bonds Between Ring Members Of The Five-membered Hetero Ring Patents (Class 548/560)
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Patent number: 5256796Abstract: There is provided a method for the preparation of 2-aryl-5-trifluoromethylpyrrole compounds via the reaction of an appropriate haloenamine and alkyl trifluoroacetoacetate. The pyrrole compounds produced are useful as insecticidal, acaricidal and nematocidal agents and as intermediates in the manufacture of said agents.Type: GrantFiled: December 11, 1992Date of Patent: October 26, 1993Assignee: American Cyanamid CompanyInventor: Venkataraman Kameswaran
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Patent number: 5254713Abstract: Novel 2- or 3-chloropyrroles represented by the general formula: ##STR1## wherein R.sup.1 represents hydrogen atom, chlorine atom, alkyl group, or aryl group which may optionally be substituted, with the proviso that any one of the two groups represented by R.sup.1 is chlorine atom,R.sup.2 represents alkyl group or aryl group which may optionally be substituted, andR.sup.3 represents tertiary alkyl group which may be substituted by phenyl, or phenyl which may optionally be substituted, andprocesses for preparing the same.Type: GrantFiled: February 10, 1993Date of Patent: October 19, 1993Assignee: Nihon Bayer Agrochem K.K.Inventors: Shinzo Kagabu, Itsumi Kawai, Katsuaki Wada
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Patent number: 5250546Abstract: Amino-alcohol derivatives of the formula, ##STR1## where R.sub.1 is a straight or branched alkyl group having 3 to 8 carbon atoms, R.sub.2 and R.sub.3 are each a lower alkyl group, or R.sub.2 and R.sub.3 form a 5- to 7-membered ring together with the adjacent nitrogen atom which may have an oxygen atom attached thereto, R.sub.4 is a hydrogen atom or a lower alkyl group, R.sub.5 is a hydrogen atom or a lower alkyl group, X is a hydrogen or halogen atom or a lower alkyl or lower alkoxy group, and n is an integer of 2 or 3, and acid addition salts thereof, are effectively useful as medicines and agricultural chemicals. Processes are also disclosed for preparing such compounds.Type: GrantFiled: July 11, 1990Date of Patent: October 5, 1993Assignee: Nippon Chemiphar Co., Ltd.Inventors: Mitsuo Masaki, Haruhiko Shinozaki, Masaru Satoh, Naoya Moritoh, Koichi Hashimoto, Toshiro Kamishiro
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Patent number: 5229524Abstract: Bis- and tris(trifluoromethyl)arylpyrrole compounds which are effective for the control of insects and acarids are described. A method for the insecticidal and acaricidal use of said compounds and methods for the preparation of said compounds are presented.Type: GrantFiled: October 13, 1992Date of Patent: July 20, 1993Assignee: American Cyanamid CompanyInventors: Venkataraman Kameswaran, Victor M. Kamhi
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Patent number: 5225568Abstract: There is provided a process for the preparation of 2-aryl-3-substituted-5-(trifluoromethyl)pyrrole compounds which are useful as insecticidal, acaricidal and nematicidal agents.Type: GrantFiled: November 25, 1992Date of Patent: July 6, 1993Assignee: American Cyanamid CompanyInventor: Venkataraman Kameswaran
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Patent number: 5223530Abstract: Novel arylcycloalkanepolyalkylamines useful as anti-psychotic, anti-ischemia, anti-stroke, anti-dementia and anti-convulsant agents. These arylcycloalkanepolyalkylamines are selective high-affinity ligands to the sigma binding-sites containing three basic units: arylcycloalkyl group, an amine group and an intermediate chain. Their preparation and use for treatment of psychoses, ischemia, stroke, dementia and convulsions are also disclosed.Type: GrantFiled: September 12, 1991Date of Patent: June 29, 1993Assignee: SRI, InternationalInventor: Daniel W. Parish
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Patent number: 5220020Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.Type: GrantFiled: November 14, 1991Date of Patent: June 15, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
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Patent number: 5210218Abstract: Novel 2- or 3-chloropyrroles represented by the general formula: ##STR1## wherein R.sup.1 represents hydrogen atom, chlorine atom, alkyl group, or aryl group which may optionally be substituted, with the proviso that any one of the two groups represented by R.sup.1 is chlorine atom,R.sup.2 represents alkyl group or aryl group which may optionally be substituted, andR.sup.3 represents tertiary alkyl group which may be substituted by phenyl, or phenyl which may optionally be substituted, andprocesses for preparing the same.Type: GrantFiled: October 15, 1991Date of Patent: May 11, 1993Assignee: Nihon Bayer Agrochem K.K.Inventors: Shinzo Kagabu, Itsumi Kawai, Katsuaki Wada
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Patent number: 5182348Abstract: Compounds of the formula (1) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 have the meanings given in the description, and the other radicals have the following meanings:X, Y and Z denote identical or different divalent radicals --O--, --S--, --N(R.sup.9)-- or --C(R.sup.10).dbd.C(R.sup.11)--, with the proviso that at least one of the radicals, X, Y and Z is not a radical of the formula --C(R.sup.10).dbd.C(R.sup.11)--, and whereinR.sup.9 is a hydrogen atom, a branched or unbranched C.sub.1 - to C.sub.8 -alkyl radical or an optionally substituted phenyl radical, andR.sup.10 and R.sup.11 are, in each case, identical or different radicals which have one of the meanings of R.sup.1,R.sup.7 and R.sup.8 denote identical or different radicals, that is to say hydrogen atoms or C.sub.1 - to C.sub.6 -alkyl or phenyl radicals, andn, m and o denote identical or different integers with a value of from 1 to 10.Type: GrantFiled: August 19, 1991Date of Patent: January 26, 1993Assignee: Wacker-Chemie GmbHInventors: Hermann Braeunling, Richard Becker, Georg Bloechl
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Patent number: 5157047Abstract: Bis- and tris(trifluoromethyl)arylpyrrole compounds which are effective for the control of insects and acarids are described. A method for the insecticidal and acaricidal use of said compounds and methods for the preparation of said compounds are presented.Type: GrantFiled: October 18, 1990Date of Patent: October 20, 1992Assignee: American Cyanamid CompanyInventors: Venkataraman Kameswaran, Victor M. Kamhi
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Patent number: 5116998Abstract: There is provided a process for the preparation of 2-halopyrrole-3-carbonitrile compounds which are useful as insecticidal, acaricidal and molluscicidal agents.Type: GrantFiled: April 22, 1991Date of Patent: May 26, 1992Assignee: American Cyanamid CompanyInventor: Gregory T. Lowen
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Patent number: 5108485Abstract: There are provided o-carboxy-(5-oxo-2-imidazolin-2-yl)benzoheterocyclic compounds wherein the fused heterocyclic ring system is a 5-membered ring containing one, two or three nitrogen atoms, derivatives of said benzoheterocyclic compounds and a method for the use therewith to control monocotyledonous and dicotyledonous plant species.Type: GrantFiled: August 31, 1990Date of Patent: April 28, 1992Assignee: American Cyanamid CompanyInventor: Robert F. Doehner, Jr.
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Patent number: 5057504Abstract: Pesticidal bicyclo-octanes are of the formula ##STR1## where R is a substituted or unsubstituted aliphatic or aromatic group, R' and R.sup.3 are H or a substituted or unsubstituted aliphatic or aromatic group, R.sup.2 is a substituted or unsubstituted heterocyclic group containing at least one ring nitrogen and is preferably a 3- or 4- pyridyl group, Z is CH.sub.2 CH.sub.2, CH.sub.2 O--CH.sub.2 S or COCH.sub.2 or CH(OR.sup.5)CH.sub.2 where R.sup.5 is H, alkyl, acyl or carbamoyl at Y and Y' are O or S(O).sub.m where m is 0, 1 or 2.Various methods for their preparation are described.Type: GrantFiled: August 16, 1989Date of Patent: October 15, 1991Assignee: The Wellcome Foundation LimitedInventors: Malcolm H. Black, John A. Wyatt, John B. Weston, John P. Larkin, Ian H. Smith, David A. Pulman
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Patent number: 5043349Abstract: Substituted pyrroles, pyrazoles and triazoles such as ##STR1## and their pharmaceutically suitable salts are useful as antihypertensive agents and for treatment of congestive heart failure.Type: GrantFiled: March 26, 1990Date of Patent: August 27, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Carini, David J., John J. V. Duncia, Gregory J. Wells
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Patent number: 5041556Abstract: There is provided a process for the preparation of 2-halopyrrole-3-carbonitrile compounds which are useful as insecticidal, acaricidal and molluscicidal agents.Type: GrantFiled: December 11, 1990Date of Patent: August 20, 1991Assignee: American Cyanamid CompanyInventor: Gregory T. Lowen
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Patent number: 5030735Abstract: There is provided a process for the preparation of 2-aryl-5-(trifluoromethyl)pyrrole compounds which are useful as insecticidal, acaricidal and nematicidal agents.Type: GrantFiled: July 31, 1990Date of Patent: July 9, 1991Assignee: American Cyanamid CompanyInventors: Roger W. Addor, Joseph A. Furch, David G. Kuhn
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Patent number: 5026759Abstract: 2-Substituted-1-naphthols are 5-lipoxygenase inhibitors which make them useful in the treatment of inflammation, obstructive lung diseases and/or psoriasis. Useful 2-substituent groups are alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkenyls, the groups CH.sub.2 --C.tbd.C--(CH.sub.2).sub.m R.sup.5 and CH.dbd.CH--(CH.sub.2).sub.n R.sup.5 (where m is 1-4, n is 0-3 and R.sup.5 includes phenyl, COOR.sup.9, where R.sup.9 is H or alkyl of 1-4 carbons, AR.sup.6 (where A is a methylene chain and R.sup.6 is a variety of groups including Cl, Br, I, CHO, CN, COOR.sup.9, NH.sub.2, SC(NH)NH.sub.2, phenyl, P(O)(OR.sup.9).sub.2, etc.), and CHR.sup.7 R.sup.21 (where R.sup.7 is a variety of aromatic and heterocyclic groups and R.sup.21 is H, optionally substituted phenyl and a variety of heterocyclic groups).Type: GrantFiled: December 4, 1989Date of Patent: June 25, 1991Assignee: Du Pont Merck PharmaceuticalInventor: Douglas G. Batt
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Patent number: 5015644Abstract: Certain substituted urea, thiourea, carbamate, and thiocarbamate compounds are potent inhibitors of the enzyme acyl-CoA: cholesterol acyltransferase and are thus useful agents for inhibiting the intestinal absorption of cholesterol, and for lowering blood plasma cholesterol.Type: GrantFiled: June 1, 1989Date of Patent: May 14, 1991Assignee: Warner-Lambert CompanyInventors: Bruce D. Roth, Bharat K. Trivedi
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Patent number: 4999042Abstract: Compounds of the fomrula (I): ##STR1## and sterioisomers thereof, wherein X is halogen, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, alkenyl, alkynyl, aryl, amino, arylazo, heteroarylalkyl, heteroaryloxyalkyl, acylamino nitro, nitride, trifluoromethyl, -OR.sup.1, -SR.sup.1, -CO.sub.2 R.sup.2, -CONR.sup.3 R.sup.4, -COR.sup.5, -CR.sup.6 .dbd.NR.sup.7, -N.dbd.CR8R.sup.9, -SOR.sup.10 or -SO.sub.2 R.sup.11 ; W, Y and Z, which may be the same or different, are any of the atoms or groups listed for X above and, in addition, may be hydrogen atoms; or any two of the groups W, X, Y and Z, in adjacent positions on the phenyl ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; R.sup.1 is alkyl, or cycloalkyl optionally containing a heteroatom in the cycloalkyl ring, alkenyl, acyl, aryl, heteroaryl, aralkyl or heteroarylalkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.8, R.sup.9, R.sup.10 and R.sup.Type: GrantFiled: December 19, 1989Date of Patent: March 12, 1991Assignee: Imperial Chemical Industries PLCInventors: Vivienne M. Anthony, John M. Clough, Christopher R. A. Godfrey, Thomas E. Wiggins
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Patent number: 4906758Abstract: Pyrroles of the formula I ##STR1## are prepared by a process in which a dialkoxytetrahydrofuran of the formula II ##STR2## where R.sup.2 to R.sup.5 in the formulae (I) and (II) are identical or different and are each hydrogen, a straight-chain or branched alkyl or alkenyl radical of not more than 12 carbon atoms, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl or aralkyl radical of 6 to 16 carbon atoms, and two non-adjacent radicals R.sup.6 to R.sup.9 are alkoxy and the other two radicals R.sup.6 to R.sup.9 are hydrogen, is reacted with ammonia or a primary amine H.sub.2 NR.sup.1, where R.sup.1 in formula (I) is hydrogen, alkyl, aryl, alkylaryl, aralkyl or cycloalkyl, in the presence of an acidic, solid, heterogeneous catalyst. Zeolites, for example those of the pentasil type or faujasite type, or phosphates, acidic oxides, phosphoric acid or boric acid on a carrier can be used as the solid heterogeneous catalysts.Type: GrantFiled: August 12, 1988Date of Patent: March 6, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Michael Hesse, Hardo Siegel
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Patent number: 4897397Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.Type: GrantFiled: December 16, 1988Date of Patent: January 30, 1990Assignee: Schering CorporationInventors: Neng Y. Shih, David J. Blythin
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Patent number: 4873344Abstract: The present invention relates to novel indene derivatives with the general formula I: ##STR1## wherein R.sup.1 is (a) a phenyl group optionally substituted with one or two groups selected from halogen, lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulfonyl, dilower alkylamino, acylamino such as acetylamino, cyano, trifluoromethyl, trifluoromethoxy, pyrrole and dilower alkylpyrrole,(b) a polycyclic aromatic or heteroaromatic group, such as naphthalene or quinoline,(c) a heteroaromatic group such as thiophene, pyridine, and pyrrole, optionally substituted with one or more groups selected from halogen, lower alkyl, lower alkoxy, lower alkylthio, trifluoromethyl or trifluoromethoxy,R.sub.2 is selected from H, halogen, lower alkyl, benzyl, lower alkylthio, methoxy, lower alkylsulfonyl, dilower alkylsulfamoyl, acylamino such as acetylamino, benzylamino, dilower alkylamino, cyano, pyrrole, dilower alkylpyrrole, trifluoromethyl and trifluoromethoxy,R.sup.3 is CN, COOR.sup.4, --CON(R.sup.4).sub.2 or COR.sup.Type: GrantFiled: November 24, 1987Date of Patent: October 10, 1989Assignee: H. Lundbeck A/SInventors: Klaus P. Bogeso, Michael B. Sommer
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Patent number: 4857539Abstract: Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms;Z is N or HC;R is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when Z is N, R is lower-alkyl;R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; andHet is selected from specified heterocyclic groups,are useful and antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.Type: GrantFiled: June 16, 1987Date of Patent: August 15, 1989Assignee: Sterling Drug Inc.Inventors: Guy D. Diana, Philip M. Carabateas
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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: 4788187Abstract: A class of benzocyclobutene aminoalkylene ether and thioether compounds exhibiting pharmacological activity, including anti-secretory and anti-ulcerogenic activity, pharmaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions.Type: GrantFiled: February 26, 1988Date of Patent: November 29, 1988Assignee: Rorer Pharmaceutical CorporationInventors: Donald E. Kuhla, Henry F. Campbell, William L. Studt
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Patent number: 4778818Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.Type: GrantFiled: April 17, 1987Date of Patent: October 18, 1988Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
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Patent number: 4778901Abstract: Intermediates for the production of microbicidal pyrrolines of the formula ##STR1## in which R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 14 C.sub.6 -haloalkyl, and n is 0, 1 or 2, and a method of converting the pyrrolines to phytofungicidal pyrroles by oxidation with bromine or oxygen. Catalysts are provided for the oxidation with oxygen.Type: GrantFiled: June 3, 1987Date of Patent: October 18, 1988Assignee: Ciba-Geigy CorporationInventor: Pierre Martin
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Patent number: 4749701Abstract: Disclosed are an aminostyryl compound represented by Formula I: ##STR1## wherein A represents a linking group having 3 to 4 chain members; B represents an unsubstituted or substituted 5 to 6-membered monocyclic type heterocyclic residue containing 1 to 2 hetero atoms, an unsubstituted or substituted condensed heterocyclic residue which contains 5 to 6-membered monocyclic type heterocycle containing 1 to 2 hetero atoms, a naphthyl group or an alkyl group having 5 to 7 carbon atoms,a composition having leukotriene antagonism which contains an aminostyryl compound represented by Formula I as the effective ingredient, and a method of antagonizing SRS based on leukotriene antagonistic activity by employing the same.Type: GrantFiled: December 15, 1986Date of Patent: June 7, 1988Assignee: Mitsubishi Chemical Industries LimitedInventors: Yoshio Hayashi, Tomei Oguri, Masaki Shinoda, Kazuo Takahashi
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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: 4652582Abstract: Antiinflammatory 2-halo-4,5-diarylpyrroles are provided. These pyrroles have the formula: ##STR1## wherein Y.sub.1 is F, Cl, Br, or I;Y.sub.2 is H, Cl, or Br;R.sub.1 is H, CH.sub.3, C.sub.2 H.sub.5, acetyl, or ##STR2## where R.sub.4 is methyl, ethyl, t-butyl, or benzyl; R.sub.2 is pyridyl or ##STR3## R.sub.3 is pyridyl or ##STR4## X and X' are independently H, F, Cl, Br, OR.sub.5, or R.sub.5 S(O).sub.n where n is 0, 1 or 2 and R.sub.5 is C.sub.1 -C.sub.2 alkyl; provided that one of R.sub.2 or R.sub.3 must be ##STR5## or a pharmaceutically suitable salt thereof. Intermediates to the above pyrroles are provided where R.sub.1 in the above formula is replaced by R.sup.1 which is benzenesulfonyl or 4-toluenesulfonyl.Type: GrantFiled: January 9, 1985Date of Patent: March 24, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Wendell W. Wilkerson
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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: 4634713Abstract: Certain 3-(ureidocyclohexyleneamino)propane-1,2-diol derivatives, such as the compounds of formula III below, represent novel and useful pharmaceutical agents, e.g. potent antihypertensive and cardioactive agents demonstrating both .alpha.- and .beta.-adrenergic blocking activity. ##STR1## R.sub.3 is hydrogen or lower alkyl; R.sub.7 is cyano, lower alkoxycarbonyl, pyrrolyl, morpholino, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, alkoxy of 1 to 3 carbon atoms substituted by cyclopropyl.Type: GrantFiled: August 19, 1985Date of Patent: January 6, 1987Assignee: Ciba-Geigy CorporationInventors: Lincoln H. Werner, Neville Ford
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Patent number: 4634783Abstract: Amidine compounds of the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful anti-trypsin, anti-plasmin, anti-kallikrein and anti-thrombin agents. They are also useful as a powerful anti-complement agent.Type: GrantFiled: January 23, 1984Date of Patent: January 6, 1987Assignee: Torii & Co. Ltd.Inventors: Setsuro Fujii, Toyoo Nakayama, Shigeki Nunomura, Ryoji Matsui, Shin-ichi Watanabe, Kimio Sudo, Toshiyuki Okutome, Masateru Kurumi, Yojiro Sakurai, Takuo Aoyama
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Patent number: 4632935Abstract: OMEGA-(Hydroxy, ether and ester) alkyl-2-Amino-Cycloalkenyl and -cycloalkyl amide compounds of the formula: ##STR1## where the wavy line bonds, m, n, p, A, R, R.sub.1, R.sub.2, X, Y and Z are as defined in the specification, e.g., 3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-3-(3-acetyloxypropyl)cyclohexe nyl]benzamide, and pharmacologically acceptable salts thereof, are useful as analgesic drug compounds having low physical dependence liability, compared to morphine and methadone. Pharmaceutical compositions and methods for using these compounds and compositions as analgesics are disclosed. Processes for preparing this class of compounds are also disclosed.Type: GrantFiled: May 30, 1984Date of Patent: December 30, 1986Assignee: The Upjohn CompanyInventor: Lester J. Kaplan
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Patent number: 4620055Abstract: The present invention provides a novel process for the preparation of styrene, stilbene, and/or substituted derivatives thereof. The process involves the reaction of an aryl sulfonyl chloride with an olefinic compound in the presence of a catalytic amount of a metal catalyst consisting essentially of palladium.Type: GrantFiled: October 7, 1985Date of Patent: October 28, 1986Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, James R. Overton, David D. Cornell
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Patent number: 4588719Abstract: A class of bicyclic benzenoid aminoalkylene ether and thioether compounds exhibiting pharmacological activity, including anti-secretory and anti-ulcerogenic activity, pharmaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions.Type: GrantFiled: October 24, 1984Date of Patent: May 13, 1986Assignee: William H. Rorer, Inc.Inventors: William L. Studt, Donald E. Kuhla, Henry F. Campbell
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Patent number: 4567265Abstract: Cyclopropanoid cyanoesters of the formula: ##STR1## where R' is --CH.sub.3 or --CH.sub.2 CH.sub.3, and A is (a) --H, or(b) A, B represents an aliphatic group joined to a carbon atom on the cyclopropanoid ring, thereby forming a spiro group, A, B being selected from structures having the formula:(i) --(CH.sub.2).sub.n --, wherein n=3, 4, or 5, and(ii) --(CH.sub.2).sub.2 --Y--(CH.sub.2).sub.2 --, wherein Y is NCH.sub.3, O, or S); and,when A is --H, B is selected from the group consisting of: ##STR2## are disclosed. These compositions are useful in the synthesis of pyrethroids. A process for synthesis of cyclopropanoid cyanoesters by reacting 2-nitropropane with cyanoesters of the general formula: ##STR3## is also disclosed and claimed.Type: GrantFiled: January 16, 1984Date of Patent: January 28, 1986Assignee: Loyola University of ChicagoInventor: James H. Babler
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Patent number: 4560769Abstract: Pyrroles are prepared by a process in which ammonia or an amine is reacted with a but-2-ene-1,4-diol in the presence of a supported catalyst containing copper, silver, zinc, palladium, nickel, cobalt and/or platinum and/or compounds of these metals as catalytic materials, and in the presence or absence of compounds of chromium and/or manganese as additional catalysts, in the gas phase.The pyrroles obtainable by the process of the invention are useful starting materials for the preparation of dyes, corrosion inhibitors, drugs and pesticides.Type: GrantFiled: March 9, 1984Date of Patent: December 24, 1985Assignee: BASF AktiengesellschaftInventors: Helmuth Menig, Martin Fischer, Karl Baer
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Patent number: 4559354Abstract: The invention relates to novel substituted phenyl ethers of the formula ##STR1## in which Ar represents a mono- or bi-cyclic carbocyclic aryl radical, or a mono- or bi-cyclic heterocyclic aryl radical bonded to a phenylene radical by way of a ring carbon atom,Ph represents a phenylene radical,n has the value 0 to 1 andalk represents alkylene having from 2 to 5 carbon atoms, the nitrogen atom and the oxygen atom or, if n is 0, the aromatic radical being separated from each other by at least two carbon atoms in the unbranched chain, andR.sub.1 and R.sub.2 each represents, independently of the other, hydrogen or lower alkyl, or together represent lower alkylene, oxa-lower alkylene, thia-lower alkylene, aza-lower alkylene or N-lower alkyl-aza-lower alkylene,and salts thereof, especially pharmaceutically acceptable non-toxic acid addition salts. Such compounds possess, on the one hand, blocking properties towards .beta.-adrenergic receptors and can therefore be used as .beta.Type: GrantFiled: May 6, 1983Date of Patent: December 17, 1985Assignee: Ciba-Geigy CorporationInventors: Walter Fuhrer, Franz Ostermayer, Markus Zimmermann
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Patent number: 4518799Abstract: Novel processes for making arylpropionic acids are described. One process comprises carboxylating particular Grignard compounds which are the products of a catalyzed reaction between corresponding arylmagnesium bromides and ethylene. Furthermore, the reaction making the particular Grignard compounds is itself novel. Also, an improved method is disclosed for making coupled aryl compounds useful as intermediates for making compounds having a pharmaceutical use. For example, particular biaryls may be used to make some of the Grignard compounds herein from which the arylpropionic acids are made. Finally, an improved bromination is disclosed giving high yields of 4-bromo-2-fluoroaniline, which is thereafter coupled with benzene, then used to make the arylmagnesium bromide reacted with ethylene to obtain the particular Grignard compound and subsequent desired arylpropionic acid, i.e. 2-(2-fluoro-4-biphenylyl)propionic acid.Type: GrantFiled: June 8, 1982Date of Patent: May 21, 1985Assignee: The Upjohn CompanyInventor: Thomas A. Hylton
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Patent number: 4477463Abstract: Antiinflammatory and/or analgesic 1-alkyl-4,5-diaryl-2-fluoroalkyl-1H-pyrroles, such as 4,5-bis(4-methoxyphenyl)-1-methyl-2-trifluoromethyl-1H-pyrrole, useful for treating arthritis and related diseases and/or relieving pain.Type: GrantFiled: May 10, 1982Date of Patent: October 16, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Saul C. Cherkofsky
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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: 4454158Abstract: Compounds of the formula ##STR1## wherein: R is phenyl, phenyl monosubstituted, disubstituted, or trisubstituted by (C.sub.1 -C.sub.8) alkyl, (C.sub.1 -C.sub.8)alkoxy, hydroxy, chlorine, bromine, iodine, fluorine, trifluoromethyl, nitro, (C.sub.1 -C.sub.6)alkylcarbonyl, benzoyl, or phenyl; 1-, or 2-naphthyl; 1-, 2-, or 3-indenyl; 1-, 2-, or 9-fluorenyl; 1-, 2-, or 3-piperidinyl; 2- or 3-pyrrolyl; 2- or 3-thienyl; 2- or 3-furanyl; 2- or 3- indolyl; 2- or 3-thianaphthenyl; or 2- or 3-benzofuranyl;R.sub.1 is hydrogen, (C.sub.1 -C.sub.8)alkyl, benzyl, or phenethyl;X and Y independently, are hydrogen, fluorine, chlorine, or bromine; andA is a divalent radical of the formula: ##STR2## wherein R.sub.2 is hydrogen, methyl, or ethyl, and m and n, independently, are an integer from 0 to 4, provided that m+n cannot be greater than 4; --(CH.sub.2).sub.p --D--(CH.sub.2).sub.Type: GrantFiled: June 1, 1981Date of Patent: June 12, 1984Assignee: Merrell Toraude et CompagnieInventor: Philippe Bey
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Patent number: 4423234Abstract: Improved yields of biaromatic compounds, e.g., unsymmetrical biphenyl compounds, result by incorporating metallic copper in a non-aqueous diazonium-type coupling reaction.Type: GrantFiled: May 17, 1982Date of Patent: December 27, 1983Assignee: FMC CorporationInventors: Ernest L. Plummer, David E. Seelye
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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: 4401545Abstract: Electrically conductive complexes of polypyrroles with nitroaromatic anions are prepared by polymerizing pyrrole, an N-alkylpyrrole and/or an N-arylpyrrole by anodic oxidation in a polar solvent, in the presence of a salt of an acidic nitroaromatic compound.Type: GrantFiled: December 21, 1981Date of Patent: August 30, 1983Assignee: BASF AktiengesellschaftInventors: Herbert Naarmann, Dieter Naegele, Klaus Penzien, Johannes Schlag, Volker Kiener, Hugo Boehm
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Patent number: 4347187Abstract: 5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein: X is hydrogen, lower alkyl, chloro or bromo; Ar is a moiety selected from the group consisting of ##STR2## in which: Y is oxygen or sulfur;R is hydrogen, methyl, chloro, or bromo, the R substitution being at the 3, 4 or 5 position of the ring;R.sup.1 is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, lower alkylcarbonyl, fluoro, chloro or bromo, the R.sup.1 substitution being at any available position in the ring;R.sup.2 is hydrogen or lower alkyl; are prepared by .beta.-decarboxylation of the corresponding dialkyl-1,1-dicarboxylates. Certain substituted pyrroles are useful as intermediates for preparing the compounds of formula I.Type: GrantFiled: June 11, 1981Date of Patent: August 31, 1982Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Robert Greenhouse
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Patent number: 4347186Abstract: 5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein: X is hydrogen or lower alkyl; Ar is a moiety selected from the group consisting of ##STR2## in which: Y is oxygen or sulfur;R is hydrogen, methyl, chloro, or bromo, the R substitution being at the 3, 4 or 5 position of the ring;R.sup.1 is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, lower alkylcarbonyl, fluoro, chloro or bromo, the R.sup.1 substitution being at any available position in the ring;R.sup.2 is hydrogen or lower alkyl;are prepared by .beta.-decarboxylation of the corresponding dialkyl-1,1-dicarboxylates. Certain substituted pyrroles are useful as intermediates for preparing the compounds of formula I.Type: GrantFiled: October 20, 1980Date of Patent: August 31, 1982Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Robert Greenhouse
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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: 4329464Abstract: The invention relates to spiro[dihydrobenzofuran-piperidines and -pyrrolidines] of the formula ##STR1## wherein R is the hydrogen atom, alkyl, alkoxycarbonyl, phenoxycarbonyl, cyano, and alkyl, alkanoyl, aralkanoyl, hydroxyalkyl, benzoylalkyl, ##STR2## where p is an integer of 2 or 3 and R.sub.1 and R.sub.2 are the same or different and are hydrogen and alkyl; X is hydrogen and alkyl; Hal is a halogen and q is an integer of 0 or 1; m is an integer of 1 or 2, n is an integer of 1, 2 or 3, where the sum of m and n is 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: May 20, 1981Date of Patent: May 11, 1982Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Richard C. Effland, Larry Davis, Joseph T. Klein