Plural Rings In A Substituent E Patents (Class 564/221)
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Patent number: 6706765Abstract: Aminoguanidine and alkoxyguanidine compounds, including compounds of the formula: wherein X is O or NR9 and R1-R4, R6-R9, R11, R12, Ra, Rb, Rc, Y, Z, n and m are set forth in the specification, as well as hydrates, solvates or pharmaceutically acceptable salts thereof, that inhibit proteolytic enzymes such as thrombin are described. Also described are methods for preparing the compounds of Formula I. The novel compounds of the present invention are potent inhibitors of proteases, especially trypsin-like serine proteases, such as chymotrypsin, trypsin, thrombin, plasmin and factor Xa. Certain of the compounds exhibit antithrombotic activity via direct, selective inhibition of thrombin, or are intermediates useful for forming compounds having antithrombotic activity.Type: GrantFiled: February 6, 2003Date of Patent: March 16, 2004Assignee: 3-Dimensional Pharmaceuticals, Inc.Inventors: Bruce E. Tomczuk, Richard M. Soll, Tianbao Lu, Cynthia L. Fedde, Carl R. Illig, Thomas P. Markotan, Thomas P. Stagnaro
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Patent number: 6518310Abstract: Aminoguanidine and alkoxyguanidine compounds, including compounds of the formula: wherein X is O or NR9 and R1-R4, R6-R9, R11, R12, Ra, Rb, Rc, Y, Z, n and m are set forth in the specification, as well as hydrates, solvates or pharmaceutically acceptable salts thereof, that inhibit proteolytic enzymes such as thrombin are described. Also described are methods for preparing the compounds of Formula I. The novel compounds of the present invention are potent inhibitors of proteases, especially trypsin-like serine proteases, such as chymotrypsin, trypsin, thrombin, plasmin and factor Xa. Certain of the compounds exhibit antithrombotic activity via direct, selective inhibition of thrombin, or are intermediates useful for forming compounds having antithrombotic activity.Type: GrantFiled: March 16, 2001Date of Patent: February 11, 2003Assignee: 3-Dimensional Pharmaceuticals, Inc.Inventors: Bruce E. Tomczuk, Richard M. Soll, Tianbao Lu, Cynthia L Fedde, Carl R Illig, Thomas P. Markotan, Thomas P Stagnaro
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Patent number: 6472563Abstract: A method of preparation of a highly pure salt of R,R-formoterol L-tartrate is disclosed. The process provides the most thermodynamically stable polymorph by recrystallization of a novel polymorph.Type: GrantFiled: November 9, 2001Date of Patent: October 29, 2002Assignee: Sepracor Inc.Inventors: Gerald J. Tanoury, Chris H. Senanayake, Donald W Kessler
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Patent number: 6423714Abstract: The compounds of formula I are useful in treating gastrointestinal disorders associated with antagonizing the motilin receptor. The compounds compete with erythromycin and motilin for the motilin receptor. In addition the compounds are antagonists of the contractile smooth muscle response to those ligands.Type: GrantFiled: March 9, 2001Date of Patent: July 23, 2002Assignee: Ortho McNeil-Pharmaceutical, Inc..Inventors: Robert H. Chen, Min A. Xiang
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Patent number: 6423870Abstract: The invention concerns compounds of formula (I) in which: A forms a tricyclic system of formula A1, A2, A3 or A4; R1 represents a hydrogen atom, an alkyl, hydroxy, alkoxy or oxo group; (R2)m and (R3)m′ are such as defined in the description; n represents an integer such that 0≦n≦3; p represents an integer such as defined in the description; B represents a group (a) or (b). The invention is useful for preparing medicines.Type: GrantFiled: July 14, 2000Date of Patent: July 23, 2002Assignee: Les Laboratoires ServierInventors: Michel Langlois, Monique Mathe-Allainmat, Carole Jellimann, Jean Andrieux, Caroline Bennejean, Pierre Renard, Philippe Delagrange
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Patent number: 6350902Abstract: The instant invention provides a process for the selective N-formylation of N-hydroxylamines.Type: GrantFiled: March 30, 2001Date of Patent: February 26, 2002Assignee: Abbott LaboratoriesInventors: David R. Hill, Chi-Nung Hsiao, Ravi Kurukulasuriya, Steve Wittenberger
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Patent number: 6268533Abstract: A method is disclosed for the preparation of optically pure isomers of formoterol by the reaction of an optically pure 4-benzyloxy-3-formamidostyrene oxide with an optically pure 4-methoxy-&agr;-methyl-N-(phenylmethyl)benzeneethanamine followed by debenzylation. Useful intermediates in the process are also disclosed, as are the novel L-tartrate salt of R,R-formoterol and pharmaceutical compositions thereof.Type: GrantFiled: January 27, 2000Date of Patent: July 31, 2001Assignee: Sepracor Inc.Inventors: Yun Gao, Robert Hett, Kevin Q. Fang, Stephen A. Wald, Chris Hugh Senanayake
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Patent number: 6262308Abstract: The invention relates to a process for preparing cis-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthylamine, or racemic sertraline, corresponding to formula (I) in salt form, starting with 4-(3,4-dichlorophenyl)tetralone of formula (II) according to which (a) the 4-(3,4-dichlorophenyl)tetralone of formula (II) is reacted with N-methylformamide in the presence of formic acid, (b) the reaction medium obtained according to (a) is treated with a base, and (c) the racemic sertraline salt is separated out by selective crystallization with an acid. The invention also relates to N-methylformamide-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthylamine and to its use to obtain racemic sertraline.Type: GrantFiled: March 29, 1999Date of Patent: July 17, 2001Assignee: CatalysInventor: Patrick Bigot
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Patent number: 6225499Abstract: This invention provides a process for preparing aminoarylacetylenes comprising reacting a N-arylmethylidene aminoarylhalide with a terminal acetylene in the presence of a base and a catalyst system comprising a palladium catalyst and a cuprous salt to produce a novel N-arylmethylidene aminoarylacetylene, and hydrolyzing the N-arylmethylidene aminoarylacetylene to the aminoarylacetylene. In one embodiment, the invention provides a process for preparing aminophenylacetylenes comprising reacting a N-benzylidene aminophenylhalide with a terminal acetylene in the presence of a base and the catalyst system to produce a novel N-benzylidene aminophenylacetylene, and hydrolyzing the N-benzylidene aminophenylacetylene to the aminophenylacetylene.Type: GrantFiled: July 14, 1997Date of Patent: May 1, 2001Assignee: Catalytica Pharmaceuticals, Inc.Inventor: John M. Gruber
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2-aminopropane-1,3-diol compounds, medicinal use thereof, and intermediates in synthesizing the same
Patent number: 6214873Abstract: The present invention relates to a compound of the general formula wherein R1, R2, R3 and R4 are each a hydrogen or an acyl, a pharmaceutically acceptable acid addition salt thereof or a hydrate thereof; a pharmaceutical comprising this compound; a pharmaceutical composition comprising this compound and a pharmaceutically acceptable carrier; and 2-amino-2-(2-(4-(1-hydroxy-5-phenylpentyl)phenyl)ethyl)propane-1,3-diol or 2-amino-2-(2-(4-formylphenyl)ethyl)propane-1,3-diol, the derivatives of the two compounds whose amino group and/or hydroxy group are(is) protected or a salt thereof. The compound of the present invention shows superior immunosuppressive action with less toxicity and higher safety, and is useful as a drug for prevention or suppression of rejection of organs or bone marrow transplantation, or as a drug for prevention or treatment of various autoimmune diseases or allergic diseases.Type: GrantFiled: January 5, 2000Date of Patent: April 10, 2001Assignee: Welfide CorporationInventors: Kunitomo Adachi, Yoshiyuki Aoki, Tokushi Hanano, Koji Teshima, Yukio Hoshino, Tetsuro Fujita -
Patent number: 6156801Abstract: A 2-phenoxyaniline derivative represented by the formula: ##STR1## wherein R.sup.1 is a hydrogen atom, an amino group or an NHCOR.sup.3 group, R.sup.2 is a halogen atom, an amino group, a cyano group, a C.sub.1-6 alkyl group, a C.sub.1-3 perfluoroalkyl group, an NHCOR.sup.3 group, a CH.sub.2 OR.sup.4 group, an OCH.sub.2 R.sup.5 group or a COR.sup.6 group, R.sup.3 is a C.sub.1-6 alkyl group, R.sup.4 is a hydrogen atom or a C.sub.1-6 alkyl group, R.sup.5 is a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.1-5 aminoalkyl group, a C.sub.2-7 alkoxy-carbonyl group or a carbamoyl group, and R.sup.6 is a C.sub.1-6 alkyl group or a C.sub.3-8 cycloalkyl group which is unsubstituted or substituted by a halogen atom, an amino group, a cyano group or a straight or branched C.sub.1-6 alkyl group; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: September 15, 1999Date of Patent: December 5, 2000Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Tomomi Ota, Misa Nakanishi, Minoru Taguchi, Kazuyuki Tomisawa
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Patent number: 6100429Abstract: This invention provides a process for preparing aminoarylacetylenes comprising reacting a N-arylmethylidene aminoarylhalide with a terminal acetylene in the presence of a base and a catalyst system comprising a palladium catalyst and a cuprous salt to produce a novel N-arylmethylidene aminoarylacetylene, and hydrolyzing the N-arylmethylidene aminoarylacetylene to the aminoarylacetylene.Type: GrantFiled: June 16, 1999Date of Patent: August 8, 2000Assignee: Catalytica Pharmaceuticals, Inc.Inventor: John M. Gruber
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Patent number: 6096925Abstract: Disclosed is a photo-curable antifogging composition which may be applied to substrates such as glass, various plastic materials and the like to give antifogging property on the surface of these substrates. The main ingredient of the composition is a quaternary ammonium salt of the following formula (1): wherein:R.sup.1 is CH.sub.3 (CH.sub.2).sub.n CH.sub.2 or CH.sub.3 (CH.sub.2).sub.n CH.sub.2 C.sub.6 H.sub.4 wherein n is an integer from 1 to 16 inclusive;R.sup.2 and R.sup.3 are the same or different from each other, and represent CH.sub.2 .dbd.C(CH.sub.3)COOCH.sub.2 CH(OH)CH.sub.2, CH.sub.2 .dbd.CHCOOCH.sub.2 CH(OH)CH.sub.2 or H, with the proviso that R.sup.2 and R.sup.3 may not be H at the same time;R.sup.4 is H, CH.sub.3, CH.sub.3 CH.sub.2 or CH.sub.3 CH.sub.2 CH.sub.2 ; andX is CH.sub.3 OSO.sub.3, CH.sub.3 CH.sub.2 OSO.sub.3, CH.sub.3 COO, CF.sub.3 COO, CH.sub.3 (CH.sub.2).sub.n COO wherein n is an integer from 1 to 16 inclusive, CH.sub.3 (CH.sub.2).sub.7 CH.dbd.CH(CH.sub.2).sub.7 COO, C.sub.6 H.sub.Type: GrantFiled: June 1, 1998Date of Patent: August 1, 2000Assignee: Ventree Co., Ltd.Inventors: Haeng-Woo Lee, Young-Hoon Park, Sang-Keun Kim, Eun-A Shin
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Patent number: 5959146Abstract: Novel tricyclic compounds of formula I as defined in the specification, a process for their preparation and their use for the preparation of optically active or racemic colchicine and thiocolchicine derivatives.Type: GrantFiled: December 13, 1996Date of Patent: September 28, 1999Assignee: Hoechst Marion RousselInventors: Francis Brion, Bernadette Chappert, Christian Diolez, Christian Marie, Alain Mazurie, Michel Middendorp, Didier Pronine, Edmond Toromanoff
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Patent number: 5866611Abstract: Compounds of formula I, and their pharmaceutically acceptable salts, ##STR1## in which R.sup.1 and R.sup.2 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, phenylalkyl or alkenyl; or NR.sup.1 R.sup.2 is a heterocyclic group; A is trimethylene optionally substituted by alkyl and the phenyl ring is optionally substituted by substituents such as halogeno, alkenyl, amino, cyano, ureido, alkyl, carbamoylalkyl, alkanoylamino, alkoxycarbonyl, N-alkyl-alkanoylamino, alkanoyl and amines thereof; are inhibitors of squalene synthese and hence useful in treating diseases in which a lowering of cholesterol is desirable. As well as the use of these compounds in medicine, novel compounds, processes for their preparation and pharmaceutical compositions are also referred to.Type: GrantFiled: May 19, 1994Date of Patent: February 2, 1999Assignee: Zeneca LimitedInventors: George Robert Brown, Murdoch Allan Eakin, Peter John Harrison, deceased, Keith Blakeney Mallion
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Patent number: 5834521Abstract: Tetracyclic compounds having the following structure are described: ##STR1## wherein R.sub.1 -R.sub.10 are as defined. The tetracyclic compounds are capable of potent effects on steroid sensitive tissues and have demonstrated increased uterine weight, antiovulatory effects and potent steroid receptor binding. The compounds have therapeutic utility in reproductive applications such as fertility control, labor induction, ovulation induction and spermatogenesis. Methods for preparing the tetracyclic compounds from substituted indanones are also described.Type: GrantFiled: August 5, 1996Date of Patent: November 10, 1998Assignee: Ortho Pharmaceutical CorporationInventors: John H. Dodd, Lisa A. Dixon, James L. Bullington, Charles F. Schwender
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Patent number: 5739374Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: February 14, 1997Date of Patent: April 14, 1998Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5739337Abstract: Disclosed are a process and novel compounds useful for preparing compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, inorganic or optionally substituted organic substituents; andR.sub.3 is hydrogen, or an optionally substituted organic group,the process comprising cyclizing a tetrahydroisoquinoline of the formula ##STR2## where Y is a leaving group, in the presence of a stong base. The invention also encompasses a process for preparing the tetrahydroisoquinoline; and a process for converting the tetrahydroisoquinoline to the final amide I.Type: GrantFiled: March 8, 1996Date of Patent: April 14, 1998Assignee: Neurogen CorporationInventor: Philip D. Magnus
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Patent number: 5712312Abstract: The invention relates to a compound selected from these of formula (I): ##STR1## in which R.sub.7, R.sub.8, Y, n and A are as defined in the description, and medicinal product containing the same useful for treating a disorder of the melatoninergic system.Type: GrantFiled: April 12, 1996Date of Patent: January 27, 1998Assignee: Adir et CompagnieInventors: Michel Langlois, Monique Mathe-Allainmat, Philippe Delagrange, Pierre Renard, Beatrice Guardiola
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Patent number: 5674812Abstract: 5-(Sulfo-/carbamoylmethyl)cyclohexenone oxime ethers I ##STR1## where R.sup.1 =C.sub.1 -C.sub.6 -alkyl;R.sup.2 =H, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.3 -alkoxy-C.sub.1 -C.sub.3 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl;R.sup.3 =C.sub.1 -C.sub.4 -alkylsulfonyl or C.sub.1 -C.sub.4 -alkylcarbonyl;Alk=a C.sub.2 -C.sub.4 -alkylene, C.sub.3 -C.sub.4 -alkenylene, C.sub.3 -C.sub.4 -alkynylene or C.sub.2 -C.sub.3 -alkyleneoxy chain, it being possible for each chain if desired to carry a C.sub.1 -C.sub.3 -alkyl group;X.sup.1, X.sup.2 and X.sup.3 =H, halogen, C.sub.1 -C.sub.4 -haloalkyl,and their salts and esters are described.Type: GrantFiled: March 31, 1995Date of Patent: October 7, 1997Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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Patent number: 5656619Abstract: Abstract of the Disclosure: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: June 6, 1995Date of Patent: August 12, 1997Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5604261Abstract: A compound which is selected from those of formula (I) : ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description, its optical isomers, and its addition salts thereof with a pharmaceutically-acceptable acid or base,and medicinal products containing the same which are useful for treating a disorder of the melatoninergic system.Type: GrantFiled: May 22, 1995Date of Patent: February 18, 1997Assignee: Adir Et CompagnieInventors: Michel Langlois, Pierre Renard, G erard Adam
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Patent number: 5484953Abstract: Novel o-phenylenediamines of the formula containing fluoroalkyl(ene) groups ##STR1## in which the symbols used have the meaning given in the description, processes for their preparation and their use as intermediates.Type: GrantFiled: June 3, 1994Date of Patent: January 16, 1996Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Bernd Baasner, Folker Lieb
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Patent number: 5463126Abstract: The invention provides the substantially geometrically pure cis-stereoisomeric form of a compound of formula (I) and the substantially geometrically and optically pure cis-stereoisomeric form of a compound of formula (II): ##STR1## wherein R.sup.1 is H or C.sub.1 -C.sub.4 alkyl, together with processes for their preparation. The compounds are intermediates for the preparation of the antidepressant agent known as sertraline.Type: GrantFiled: January 10, 1994Date of Patent: October 31, 1995Assignee: Pfizer Inc.Inventor: Michael T. Williams
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Patent number: 5434304Abstract: The present invention is directed to a process for preparing formoterol and related compounds and derivatives thereof and their pharmacologically and pharmaceutically acceptable fumarate salts and/or solvates. The present invention is also directed to certain formoterol related compounds per se.Type: GrantFiled: September 20, 1994Date of Patent: July 18, 1995Assignee: Aktiebolaget AstraInventors: Jan W. Trofast, Edib Jakupovic, Katarina L. Mansson
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Patent number: 5430062Abstract: The present invention relates to stilbene derivatives which possess utility as anti-cancer agents. The compounds can be used to treat cancers which are susceptible to treatment therewith, and can be utilized in a method of treating such cancers. Pharmaceutical compositions containing the compounds are disclosed. Three preferred compounds among those disclosed are (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, (Z)-1-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, and 4-methyl-3',4',5'-trimethoxybenzylaniline hydrochloride.Type: GrantFiled: June 23, 1993Date of Patent: July 4, 1995Assignee: Research Corporation Technologies, Inc.Inventors: Mark S. Cushman, Ernest Hamel
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Patent number: 5384331Abstract: 5,6-Dehydronorketamine and derivatives retaining the .alpha.,.beta.-unsaturated carbonyl are disclosed. These end other Michael or Michael-type acceptors and adducts are shown to influence the replication, differentiation or maturation of blood cells, especially platelet progenitor cells. Accordingly, these compounds are used for treatment of thrombocytopenia.Type: GrantFiled: May 28, 1993Date of Patent: January 24, 1995Assignee: Genentech, Inc.Inventors: Timothy P. Kogan, Todd C. Somers
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Patent number: 5382682Abstract: Novel aryloxy-nitroanilides of formula ##STR1## wherein R is alkyl from 1 to 5 carbon atoms or unsubstituted or substituted aryl of from 6 to 10 carbon atoms; one of R.sup.1 and R.sup.2 is a hydrogen atom and the other is aryloxy, wherein the aryl is unsubstituted or substituted with one or more alkyl of from 1 to 10 carbon atoms, with the proviso that when R is methyl, R.sup.1 may not be unsubstituted phenoxy and when R is 2-hydroxy-5-chlorophenyl, R.sup.2 may not be unsubstituted or chloro or methyl substituted phenoxy, and a method of preparing them. The compounds are suitable as intermediates for the preparation of anilines, required in the preparation of useful photographic and pharmaceutical compounds.Type: GrantFiled: August 18, 1992Date of Patent: January 17, 1995Assignee: Eastman Kodak CompanyInventors: Paul R. Buckland, Lee H. Latimer
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Patent number: 5349086Abstract: A compound of the formula ##STR1## is prepared by reacting an N-acylated-o-toluidine of the formula ##STR2## with n-alkyllithium to form a dilithio intermediate of the formula ##STR3## which can then be quenched with N-benzylidenemethylamine to form compound II. Hydrolysis of compound(II) yields the free base ##STR4## or its salt, which can be cyclized to form 4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine or its physiologically acceptable salts, which are useful as pharmacological agents.Type: GrantFiled: November 23, 1992Date of Patent: September 20, 1994Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Thomas B. K. Lee, George E. Lee
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Patent number: 5250732Abstract: 5,6-Dehydronorketamine and derivatives retaining the .alpha.,.beta.-unsaturated carbonyl are disclosed. These and other Michael or Michael-type acceptors and adducts are shown to influence the replication, differentiation or maturation of blood cells, especially platelet progenitor cells. Accordingly, these compounds are used for treatment of thrombocytopenia.Type: GrantFiled: July 18, 1991Date of Patent: October 5, 1993Assignee: Genentech, Inc.Inventors: Timothy P. Kogan, Todd C. Somers
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Patent number: 5225601Abstract: Abstract of the Disclosure: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: October 31, 1991Date of Patent: July 6, 1993Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5214202Abstract: This invention relates to a synthesis method favorable for the industrial production of a benzoic acid derivative having a retinoid activity of the general formula: ##STR1## wherein the derivative can be obtained by a simple procedure in safety with high yield.Specifically, this invention relates to a synthesis method characterized in that only one vessel is needed for several reactions in the different steps of subjecting acetanilide as a starting material, which is readily available and safe to handle, to Friedel-Crafts reaction with 2,5-dimethyl-2,5-dichlorohexane; subjecting the thus obtained compound to acyl exchange reaction with monomethyl ester terephthalic chloride, followed by hydrolysis; and recrystallizing from a mixture of methanol and water.Moreover, the crystals in novel form obtained by the synthesis method of this invention are suitable for formulation, because the amount of solvents remaining therein after recrystallization is small and the grain size thereof is uniform.Type: GrantFiled: November 6, 1991Date of Patent: May 25, 1993Assignee: Shionogi & Co., Ltd.Inventors: Yoshinori Hamada, Isamu Yamada, Masaaki Uenaka, Teruo Sakata
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Patent number: 5185465Abstract: Novel 4-phenyl-1,3-benzodiazepines and 2-amino-.alpha.-phenylphenethylamines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants. The 2-amino-.alpha.-phenylphenethylamines are useful as anticonvulsant and neuroprotective agents.Type: GrantFiled: October 16, 1990Date of Patent: February 9, 1993Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Manfred Worm, Charles A. Crichlow
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Patent number: 5173105Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: February 5, 1991Date of Patent: December 22, 1992Assignee: Imperial Chemical Industries PlcInventor: Christopher G. Knudsen
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Patent number: 5130454Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.Type: GrantFiled: December 19, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
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Patent number: 5128479Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A have the meanings specified in the description, and the preparation thereof are described. The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: January 29, 1990Date of Patent: July 7, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5114975Abstract: The invention relates to novel substituted aryloxyphenylthioureas, aryloxyphenylisothioureas and aryloxyphenylcarobodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.8 cycloalkyl, unsubstituted or substituted by one or more C.sub.1 -C.sub.3 alkyl groups; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 and R.sub.3 are each C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen, methyl or --CHO,R.sub.5 is halogen; C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by one or more halogen atoms; C.sub.1 -C.sub.4 alkoxy, unsubstituted or substituted by one or more halogen atoms; or is a --CH.dbd.CH).sub.2, --CH.sub.2).sub.3 or --CH.sub.2).sub.4 bridge in 2,3- or 3,4-position,n is 0, 1, 2, 3 or 4,Z is --NH--CS--NH--, --N.dbd.C(SR.sub.6)--NH-- or --N.dbd.C.dbd.N--; andR.sub.6 is C.sub.1 -C.sub.Type: GrantFiled: April 3, 1991Date of Patent: May 19, 1992Assignee: Ciba-Geigy CorporationInventors: Manfred Boger, Jozef Drabek, Josef Ehrenfreund
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Patent number: 5043469Abstract: Process for the introduction of functional or functionalizable substituents para to the amino group in 2-aminophenols and 3-aminophenols. The process proceeds in one step, with substitution occurring selectively at the position para to the amino group. Consequently, the reaction is surprisingly straightforward, with very little or no contamination by isomeric by-products. The process comprises reaction of (a) an aminophenol having an open para position to the amino function, with (b) an unhindered non-enolizable aldehyde, and (c) a thiol or sulfinic acid which acts as a nucleophile. In preferred embodiments, the process is conducted at a temperature of from about 50.degree. C. to about 100.degree. C., and in the presence of a polar solvent. The reaction is promoted by an acid having sufficient acidity to protonate the amino group of the aminophenol. Preferably, the acid promoter is a mineral acid, and it is present in an amount at least substantially equivalent to the amount of aminophenol reactant.Type: GrantFiled: April 13, 1990Date of Patent: August 27, 1991Assignee: Eastman Kodak CompanyInventors: Philip T. S. Lau, Danny R. Thompson
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Patent number: 5032592Abstract: A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring a is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl, and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.Type: GrantFiled: May 30, 1989Date of Patent: July 16, 1991Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, John Oldfield, Howard Tucker
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Patent number: 5026730Abstract: The invention relates to novel substituted anilinophenylthioureas, anilinophenylisothioureas and anilinophenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.8 cycloalkyl, unsubstituted or substituted by one or more C.sub.1 -C.sub.3 alkyl groups; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 and R.sub.3 are each C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen, methyl or --CHO,R.sub.5 is halogen; C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by one or more halogen atoms; C.sub.1 -C.sub.4 alkoxy, unsubstituted or substituted by one or more halogen atoms; or is a --CH.dbd.CH--.sub.2, --CH.sub.2--3 or --CH.sub.2--4 bridge in 2,3- or 3,4-position,n is 0, 1, 2, 3 or 4,Z is --NH--CS--NH--, --N.dbd.C(SR.sub.6)--NH-- or --N.dbd.C.dbd.N--; andR.sub.6 is C.sub.1 -C.sub.Type: GrantFiled: August 11, 1988Date of Patent: June 25, 1991Assignee: Ciba-Geigy CorporationInventors: Manfred Boger, Jozef Drabek, Josef Ehrenfreund
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Patent number: 5021414Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus;wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --,wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.Type: GrantFiled: December 18, 1989Date of Patent: June 4, 1991Assignee: Imperial Chemical Industries PLCInventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
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Patent number: 5001261Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2 R.sup.3, R.sup.4 and R.sup.5 have the meanings given in the disclosure, and their use for controlling unwanted plant growth.Type: GrantFiled: April 18, 1988Date of Patent: March 19, 1991Assignee: BASF AktiengesellschaftInventors: Michael Keil, Rainer Becker, Dieter Jahn, Norbert Goetz, Ulrich Schirmer, Bruno Wuerzer
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Patent number: 4980366Abstract: Novel 4'-hydroxybenzylamine derivatives of the formula ##STR1## pharmaceutical compositions and methods of use thereof are the present invention. Utility is for the treatment of arthritis, asthma, Raynaud's disease, inflammatory bowel disorders, trigeminal or herpetic neuralgia, inflammatory eye disorders, psoriasis, dental pain, and headaches, particularly vascular headache, succh as migraine, cluster, mixed vascular syndromes, as well as nonvascular, tension headaches.Type: GrantFiled: March 16, 1989Date of Patent: December 25, 1990Assignee: Warner-Lambert Co.Inventors: Graham Johnson, Michael F. Rafferty
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Patent number: 4943591Abstract: The invention provides compounds of the general formula (I) ##STR1## wherein X represents a C.sub.1-6 alkylene, C.sub.2-6 alkenylene or C.sub.2-6 alkynylene chain andY represents a bond, or a C.sub.1-4 alkylene, C.sub.2-4 alkenylene or C.sub.2-4 alkynylene chain with the proviso that the sum total of carbon atoms in X and Y is not more than 8;Ar represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms or the groups C.sub.1-3 alkyl, nitro, --(CH.sub.2).sub.q R [where R is hydroxy, C.sub.1-3 alkoxy, --NR.sup.3 R.sup.4 (where R.sup.3 and R.sup.4 each represent a hydrogen atom, or a C.sub.1-4 alkyl group, or --NR.sup.3 R.sup.4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from --O-- or --S-- or a group --NH-- or --N(CH.sub.3)--), --NR.sup.5 COR.sup.6 (where R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group, and R.sup.6 represents a hydrogen atom or a C.sub.Type: GrantFiled: October 14, 1986Date of Patent: July 24, 1990Assignee: Glaxo Group LimitedInventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor, Ian B. Campbell
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Patent number: 4933493Abstract: Novel 4-phenyl-1,3-benzodiazepines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants.Type: GrantFiled: April 6, 1989Date of Patent: June 12, 1990Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Manfred Worm, Charles A. Crichlow
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Patent number: 4921524Abstract: The invention provides compounds of the general formula ##STR1## wherein R represents a hydrogen atom, or an optionally substituted alkyl or acyl group, or an alkenyl or alkynyl group or an inorganic or organic cation;R.sup.1 represents an alkyl, haloalkyl, alkenyl, alkynyl or phenyl group;R.sup.2 represents an optionally substituted alkyl or phenalkyl group or a cycloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl group;R.sup.3 represents a hydrogen atom or an alkyl group; andone of R.sub.4 and R.sup.5 represents a hydrogen atom or an alkyl group, while the other of R.sup.4 and R.sup.5 represents an optionally substituted phenyl group; together with their use as herbicides and their preparation using novel intermediates.Type: GrantFiled: April 14, 1988Date of Patent: May 1, 1990Assignee: Shell Internationale Research Maatschappij B.V.Inventors: Terence Gilkerson, Robert W. Shaw, David C. Jennens
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Patent number: 4918236Abstract: A compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.m -wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 - C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: June 9, 1986Date of Patent: April 17, 1990Assignee: ICI Americas Inc.Inventors: Christopher G. Knudsen, William J. Michaely
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Patent number: 4886911Abstract: The invention concerns compounds of formula I ##STR1## wherein: X and Y are independently selected from the group consisting of hydrogen, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, and the group wherein X and Y together from a three or four-membered carbon bridge the bridge optionally comprising one or both of a double bond and a carbonyl group;Z is selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.4 alkyl and C.sub.1 to C.sub.4 alkanoyl;R.sup.1 is selected from the group consisting of: hydrogen; an acyl group; and an inorganic or organic cation;R.sup.2 is selected from the group consisting of: C.sub.1 to c.sub.6 alkyl; C.sub.2 to C.sub.6 alkenyl; C.sub.2 to C.sub.6 haloakenyl; C.sub.2 to C.sub.6 alkynyl; and substituted C.sub.1 to C.sub.Type: GrantFiled: June 12, 1987Date of Patent: December 12, 1989Assignee: ICI Australia LimitedInventors: Keith G. Watson, Craig G. Lovel
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Patent number: 4872902Abstract: The invention relates to the novel cyclohexanediones of formula I ##STR1## in which R is hydrogen or C.sub.1 -C.sub.6 -alkyl,A is R.sub.2, OR.sub.3 or NR.sub.3 R.sub.4,R.sub.2 is C.sub.1 -C.sub.6 -alkyl that is unsubstituted or is mono-substituted by C.sub.1 -C.sub.4 -alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, or is phenyl or benzyl each of which is unsubstituted or is mono-, di- or tri-substituted by R.sub.5,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 and R.sub.4 are, in addition, together with the nitrogen atom to which they are bonded, a pyrrolidine, morpholine or piperidine radical,B is one of the radicals ##STR2## m is 0, 1, 2 or 3, R.sub.5 is halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.Type: GrantFiled: February 8, 1988Date of Patent: October 10, 1989Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4868300Abstract: Compounds of the formula ##STR1## wherein: z is O or I;X is ##STR2## a and b are 0, 1, or 2 and a+b=0, 1 or 2; R, R.sup.1, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently hydrogen, alkyl or aralkyl;R.sub.n is hydrogen, alkyl, aralkyl, acyl, carbalkoxy, carbamyl, carbalkoxyalkyl, hydroxyalkyl, alkoxyalkyl or amidino;R.sup.5 groups on vicinal carbon atoms may together form a carbon-carbon double bond when a or b=2;R groups on vicinal carbon atoms may together form a carbon-carbon double bond when R.sub.n is hydrogen and z=1;R.sup.4 and R.sup.5 geminal groups may together form a spiro substituent, --(CH.sub.2).sub.d --, where d is 2 to 5;R.sup.5 and R.sup.6 groups may together form a carbon-nitrogen double bond when R.sub.3 is hydrogen and a+b=1;R.sup.2 is hydrogen or --(CH.sub.2).sub.y --Y where y is 1-3;Y is hydrogen, --O--R.alpha., --S-R.alpha. or ##STR3## R.alpha. is hydrogen, alkyl, cycloalkyl or acyl; R.beta. is hydrogen or alkyl; andR.alpha. and R.beta.Type: GrantFiled: July 21, 1987Date of Patent: September 19, 1989Assignee: Rorer Pharmaceutical CorporationInventors: Donald E. Kuhla, Henry F. Campbell, William L. Studt, William C. Faith, Bruce F. Molino