Nitrogen Or A -c(=x)- Group, Wherein X Is Chalcogen, Attached Directly To The Bicyclo Ring System By Nonionic Bonding Patents (Class 549/57)
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Patent number: 5760030Abstract: The instant invention provides novel benzothiophene compounds, pharmaceutical formulations, and methods of use.Type: GrantFiled: June 30, 1997Date of Patent: June 2, 1998Assignee: Eli Lilly and CompanyInventors: Henry Uhlman Bryant, George Joseph Cullinan, Kennan Joseph Fahey
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Patent number: 5755875Abstract: Compounds selected from the series consisting of the perylenecarboximide, quinacridone, isoindoline, indigoid, azo, benzodipyrrolone, benzodifuranone, furanofuran, pyrrolo?2,5-b!pyrrole and bianthraquinone chromophores containing at least one grouping of formula ##STR1## wherein each A may be N--CN or O, with the proviso that at least one A must be N--CN, X is --N(R)--, --O-- or --S--, R is hydrogen, C.sub.1 -C.sub.18 alkyl, unsubstituted or halogen- or C.sub.1 -C.sub.4 alkyl-substituted phenyl, benzyl or phenethyl, and m and n are each independently of the other 0 or 1.Depending on the nature of their substituents, these compounds can be used as polymer-soluble dyes or as pigments for coloring high molecular weight organic material. They are distinguished by a surprisingly high solid-state fluorescence.Type: GrantFiled: March 22, 1996Date of Patent: May 26, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: John S. Zambounis, Zhimin Hao, Abul Iqbal
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Patent number: 5750728Abstract: Aromatic bromomethyl compounds play a major role in the synthesis of active substances. They can be obtained in particularly pure form by the free-radical bromination of aromatic methyl compounds in the solvent chlorobenzene.Type: GrantFiled: December 11, 1996Date of Patent: May 12, 1998Assignee: Clariant GmbHInventors: Adalbert Wagner, Heinz-Werner Kleemann, Dieter Regnat, Hans-Jerg Kleiner
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Patent number: 5750691Abstract: Transformations of taxol, baccatin III and of 10-deacetyl baccatin III provide access to novel taxol analogs and key intermediates thereto.Type: GrantFiled: August 7, 1995Date of Patent: May 12, 1998Assignee: The Scripps Research InstituteInventors: K. C. Nicolaou, Philippe G. Nantermet, Rodney K. Guy, Hiroaki Ueno
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Patent number: 5750564Abstract: Compounds having anti-inflammatory and anti-oxidant activity are disclosed. The compounds are useful in preventing and treating inflammatory disorders through several mechanisms. Methods of treatment employing these properties of the compounds and corresponding pharmaceutical compositions are disclosed.Type: GrantFiled: September 12, 1995Date of Patent: May 12, 1998Inventors: Mark Hellberg, Pete Delgado, Jon C. Nixon
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Patent number: 5739396Abstract: Ligands useful for transition metal catalyzed bond forming reactions are provided with a metal binding portion having at least one metal binding moiety ##STR1## wherein Ar and Ar' each is an aryl or a heteroaryl. These ligands may be prepared by providing an aromatic carboxylic acid having a diarylphosphino or diheteroarylphosphino substituent on the aromatic ring, and forming an ester or an amide derivative of the carboxylic acid by coupling with a chiral diol or a chiral diamine. The ligands facilitate, for example, flexible strategies for enantiocontrolled construction of five membered carbocyclic rings with varying substitution patterns and high enantioselectivity.Type: GrantFiled: June 7, 1995Date of Patent: April 14, 1998Assignee: Stanford UniversityInventors: Barry M. Trost, David L. Van Vranken, Richard C. Bunt
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Patent number: 5728724Abstract: The present invention relates to compounds of formula I ##STR1## wherein R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), or --OSO.sub.2 (C.sub.4 -C.sub.6 alkyl);R.sup.2 is 1-naphthyl, 2-naphthyl, 2-thienyl, 3-thienyl, benzothienyl, or --CH.sub.2 C.sub.6 H.sub.5 ; any of which may be optionally substituted with 1-3 substituents independently selected from the group halo, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), or --OSO.sub.2 (C.sub.4 -C.sub.6 alkyl);X is --CH.sub.2 --, --CO--, or --CH(OH)--;n is 2 or 3; andR.sup.3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: August 6, 1996Date of Patent: March 17, 1998Assignee: Eli Lilly and CompanyInventors: Henry Uhlman Bryant, Timothy Alan Grese, Stephen Sung Yong Cho
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Patent number: 5712390Abstract: The present invention provides processes for preparing compounds of formula I ##STR1## and for preparing compounds of formula VII ##STR2## Also provided are processes for preparing compounds of formula VII in addition to intermediates of formula IX ##STR3## wherein R.sup.1' is --OH, or --OR.sup.3, in which R.sup.3 is a hydroxy protecting group; andZ is bromo, iodo, triflate, or --B(OH).sub.2.Type: GrantFiled: October 27, 1995Date of Patent: January 27, 1998Assignee: Eli Lilly and CompanyInventors: Kenneth L. Hauser, Alan D. Palkowitz, Daniel J. Sall, Kenneth J. Thrasher
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Patent number: 5703116Abstract: Methods and compositions for treating cancer and other diseases in which inhibition of telomerase activity can ameliorate disease symptoms or prevent or treat the disease relate to compounds that are derivatives of benzo?b!thiophenes. Such compounds are characterized by the following structure: ##STR1## In this compound, R.sub.1 is selected from the group consisting of --OR.sub.7, --NR.sub.8 R.sub.9, --NHNR.sub.10 R.sub.11, --NHNHC(X.sub.2)NHR.sub.12, --NHSO.sub.2 NR.sub.8 R.sub.9, --NHNHC(O)R.sub.12, --NHNHSO.sub.2 R.sub.12 and --NHC(O)NR.sub.8 R.sub.9. R.sub.7 -R.sub.12 are selected independently from the group consisting of hydrogen, alkyl, aryl, aralkyl, heteroaryl and heteroaralkyl. X.sub.1 and X.sub.2 are selected independently from the group consisting of oxygen and sulfur. R.sub.2 is hydrogen or halogen. R.sub.3 -R.sub.6 are selected independently from the group consisting of hydrogen, halogen, hydroxyl, --NR.sub.8 R.sub.9, nitro, cyano, alkoxyl, lower alkyl, aryl and aryloxyl.Type: GrantFiled: April 18, 1995Date of Patent: December 30, 1997Assignee: Geron CorporationInventors: Federico C. A. Gaeta, Adam Antoni Galan, Elaine C. Stracker
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Patent number: 5691359Abstract: Heterocyclylcarbonyl substituted benzofuranyl- and thiophenyl-alkanecarboxylic acid derivatives are prepared by reacting appropriately substituted hydroxybenzene butanoic acid esters with heterocyclic ketones. The inventive compounds can be used for the preparation of medicaments, particularly of medicaments for the treatment and prevention of acute and chronic inflammatory processes.Type: GrantFiled: May 23, 1995Date of Patent: November 25, 1997Assignee: Bayer AktiengesellschaftInventors: Rudiger Fischer, Gabriele Braunlich, Mazen Es-Sayed, Rudolf Hanko, Stephen Tudhope, Graham Sturton, Trevor Abram, Mary F. Fitzgerald
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Patent number: 5688826Abstract: Compounds for formula I ##STR1## in which X represents O, NR.sup.a, S, SO or SO.sub.2 and R is as defined in the specification; and non-toxic metabolically labile esters or amides thereof; and pharmaceutically acceptable salts thereof are useful as modulators of metabotropic glutamate receptor function.Type: GrantFiled: November 14, 1996Date of Patent: November 18, 1997Assignee: Eli Lilly and CompanyInventors: Steven Marc Massey, James Allen Monn, Matthew John Valli
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Patent number: 5684002Abstract: A compound having the structure: ##STR1## wherein (a) W is --C(X')--NRR' or --NR--C(X')R';(b) X and X' are independently O or S;(c) each Y is independently hydrogen or straight, branched or cyclic alkanyl having from 1 to about 3 carbon atoms, or the two Y's are bonded to form an alkanyl ring having from 3 to about 7 carbon atoms;(d) Z is unsubstituted branched or cyclic alkyl, or unsubstituted or alkanyl-substituted phenyl or benzyl, Z having from 3 to about 10 atoms other than hydrogen;(e) R and R' are each independently selected from hydrogen, hydroxy straight, branched or substituted alkyl having from 1 to about 6 carbon atoms, and cyclic alkyl having from 3 to about 7 carbon atoms; unsubstituted or substituted aryl, heteroaryl or heterocyclic groups; or R and R' are bonded together to form a ring having from from 3 to about 8 atoms wherein about 1 to about 4 atoms may be heteroatoms;pharmaceutical compositions comprising such compounds, and methods of treating inflammation or pain using such compounds.Type: GrantFiled: June 7, 1995Date of Patent: November 4, 1997Assignee: The Procter & Gamble CompanyInventors: Michael Wiard Scherz, John Michael Janusz
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Patent number: 5684041Abstract: A compound having the structure: ##STR1## wherein (a) n is from 1 to about 3;(b) X is selected from the group consisiting of O, S, SO, or SO.sub.2 ;(c) Y is independently hydrogen or straight, branched or cyclic alkyl having from 1 to about 4 carbon atoms, or the Y's are bonded together to form an alkanyl ring having from 3 to about 7 atoms;(d) Z is hydrogen or straight, branched or cyclic alkyl having from 3 to about 10 atoms other than hydrogen;(e) W is O or S; and(f) R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen, straight, branched or cyclic alkyl having from 1 to 10 carbon atoms, aryl, heterocyclyl, heteroaryl, hydroxy, or alkoxy; or R1, R2 or R3 may be bonded to form one or more rings each ring having from 3 to about 7 atoms wherein from 1 to 3 atoms may be heteroatoms.pharmaceutical compositions comprising such compounds, and methods of treating inflammation or pain using such compounds.Type: GrantFiled: February 1, 1996Date of Patent: November 4, 1997Assignee: The Procter & Gamble CompanyInventor: Michael Wiard Scherz
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Patent number: 5684031Abstract: A compound having the structure: ##STR1## wherein (a) n is from 1 to about 3;(b) X is selected from the group consisting of O, S, SO, or SO.sub.2 ; (c) Y is independently hydrogen or straight, branched or cyclic alkyl having from 1 to about 4 carbon atoms, or the Y's are bonded together to form an alkanyl ring having from about 3 to about 7 atoms;(d) Z is hydrogen or straight, branched or cyclic alkyl having from 3 to about 10 atoms other than hydrogen;(e) R.sub.1 is hydrogen or straight, branched or cyclic alkyl, aryl or C(.dbd.NH)--NHR.sub.4 ; and(f) R.sub.2, R.sub.3, and R.sub.4, are independently hydrogen, straight, branched or cyclic alkyl having from one to 10 carbon atoms, or aryl; R.sub.2 and R.sub.3 can be bonded together to form a ring having 5 or 6 atoms.pharmaceutical compositions comprising such compounds, and methods of treating inflammation or pain using such compounds.Type: GrantFiled: February 1, 1996Date of Patent: November 4, 1997Assignee: The Procter & Gamble CompanyInventors: John Michael Janusz, James Madison Ridgeway, II
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Patent number: 5674891Abstract: A compound having the structure: ##STR1## wherein (a) X is oxygen or sulfur;(b) each Y is independently hydrogen or unsubstituted straight, branched or cyclic alkanyl having from 1 to about 3 carbon atoms, or the two Y's are bonded to form an alkanyl ring having from 3 to about 7 carbon atoms;(c) Z is hydrogen or unsubstituted branched or cyclic alkyl, or unsubstituted or alkanyl-substituted phenyl, having from 3 to about 10 atoms other than hydrogen;(d) W is straight, branched or cyclic alkyl or aryl, unsubstituted or substituted, saturated or mono- or di-unsaturated with double bonds except that no terminal carbon atom of W is part of a double bond; W having from 1 to about 15 atoms other than hydrogen; pharmaceutical compositions comprising such compounds, and methods of treating inflammation or pain using such compounds.Type: GrantFiled: June 7, 1995Date of Patent: October 7, 1997Assignee: The Procter & Gamble CompanyInventors: Michael Wiard Scherz, Randall Stryker Matthews
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Patent number: 5663368Abstract: This invention relates to novel diastereomeric acid addition salts of homochiral hydroxylamines, to processes for obtaining such, to processes for the conversion thereof to the corresponding homochiral hydroxylamines, to certain novel homochiral hydroxylamines and the processes for using these as intermediates.Type: GrantFiled: April 11, 1996Date of Patent: September 2, 1997Assignee: Smithkline Beecham CorporationInventors: Joseph R. Flisak, Stephen Torey Ross
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Patent number: 5635527Abstract: A novel carboxylic acid compound having a condensed ring, which is represented by the formula (I) ##STR1## wherein each symbol is as defined in the specification, a pharmacologically acceptable salt thereof, a pharmaceutical composition thereof and pharmaceutical use thereof. The novel carboxylic acid compound having a condensed ring and pharmacologically acceptable salt thereof of the present invention have superior GPIIb/IIIa antagonism in mammals inclusive of human; can be administered orally; have long life in blood and low toxicity; and show less side-effects. Accordingly, they are extremely useful for the prophylaxis and treatment of thrombotic diseases and other diseases.Type: GrantFiled: February 6, 1996Date of Patent: June 3, 1997Assignee: The Green Cross CorporationInventors: Shinichiro Ono, Tomohiro Yoshida, Atsuyuki Ashimori, Keigo Kosaka, Takehiro Okada, Kazuhiro Maeda, Masahiro Eda, Fumio Mori, Yoshihisa Inoue, Hajime Ebisu, Teruaki Imada, Ruriko Ikegawa, Feng Wang, Norifumi Nakamura
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Patent number: 5614639Abstract: The present invention provides processes for preparing 2-substituted benzo[b]thiophene compounds, some of which are useful as intermediates for preparing pharmaceutically-active compounds and others which are useful, inter alia, for the treatment of osteoporosis in postmenopausal women.Type: GrantFiled: March 31, 1995Date of Patent: March 25, 1997Assignee: Eli Lilly and CompanyInventors: Kenneth L. Hauser, Alan D. Palkowitz, Daniel J. Sall, Kenneth J. Thrasher
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Patent number: 5614521Abstract: A compound of the formula (I): ##STR1## wherein R.sup.1 is an unsubstituted or substituted amino group, a protected amino group, or a nitro group; R.sup.2 is an unsubstituted or substituted amino group, a protected amino group, an unsubstituted or substituted hydroxy group or a protected hydroxy group; R.sup.3 is an unsubstituted or substituted amino group, m is 0 to 2; n is 0 to 6; with the proviso that when m is 0, then n is an integer from 2 to 6, and pharmaceutically acceptable salts thereof. Compounds of formula (I) except those wherein R.sup.1 is a nitro group have activity in promoting the production of nerve growth factor.Type: GrantFiled: April 24, 1995Date of Patent: March 25, 1997Assignee: Sankyo Company, LimitedInventors: Shunji Naruto, Yuichi Sugano, Keiichi Matsuda, Masahiko Sugimoto, Tomiichiro Oda
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Patent number: 5608074Abstract: An improved process for the preparation of 3-chlorobenzo[b]thiophene-2-carbonyl chlorides is described where a cinnamic acid is converted in the presence of thionyl chloride and a 4-N,N'-disubstituted aminopyridine in one step to the desired product.Type: GrantFiled: December 19, 1994Date of Patent: March 4, 1997Assignee: Warner-Lambert CompanyInventor: Jonathan Walker
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Patent number: 5608080Abstract: The present invention provides a process for producing a 2-substituted benzo[b]thiophene, which is characterized by reacting a substituted or unsubstituted 2-halogenobenzaldehyde with sulfur and a compound represented by general formula (1)H.sub.i S.sub.j M.sub.k (1)(wherein M represents an alkali metal; i represents an integer of 0 or 1; j represents an integer of 1 or more; and k represents an integer of 1-2 with a proviso that i+k=2), or with a compound of general formula (1) wherein j is 2 or more, in the presence of an aprotic polar solvent, and then reacting the reaction mixture with a compound represented by general formula (2)XCH.sub.2 R (2)(wherein X represents a halogen atom; and R represents an acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted arylcarbonyl group or a cyano group) to give rise to intramolecular ring closure.Type: GrantFiled: May 22, 1995Date of Patent: March 4, 1997Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Naoto Yazawa, Yoshinori Saito, Hidetaka Hiyoshi
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Patent number: 5606075Abstract: The present invention is directed to new processes for the synthesis of 2-aryl benzo[b]thiophenes.Type: GrantFiled: June 7, 1995Date of Patent: February 25, 1997Assignee: Eli Lilly and CompanyInventors: David W. Hoard, Wayne D. Luke
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Patent number: 5606076Abstract: The present invention is directed to a process for the synthesis of 2-arylbenzo[b]thiophenes.Type: GrantFiled: June 7, 1995Date of Patent: February 25, 1997Assignee: Eli Lilly and CompanyInventors: James A. Aikins, Tony Y. Zhang
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Patent number: 5597823Abstract: The present invention relates to a compound of the formula ##STR1## and the pharmaceutically acceptable salts thereof wherein W is a tricyclic heterocyclic ring system; which is an .alpha.-1 adrenergic antagonist and is useful in the treatment of BPH; also disclosed are .alpha.-1 antagonist compositions and a method for antagonizing .alpha.-1 receptors and treating BPH.Type: GrantFiled: June 5, 1995Date of Patent: January 28, 1997Assignee: Abbott LaboratoriesInventors: Michael D. Meyer, Robert J. Altenbach, Fatima Z. Basha, William A. Carroll, Irene Drizin, Steven W. Elmore, James F. Kerwin, Jr., Suzanne A. Lebold, Edmund L. Lee, Kevin B. Sippy, Karin R. Tietje, Michael D. Wendt
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Patent number: 5597918Abstract: A fused pyridazine compound of the formula ##STR1## wherein each symbol is as defined in the description. The compounds of the present invention are useful as anxiolytic agents which selectively act on anxiety because of having less side effects (e.g. muscle-relaxation, sedation or interaction with alcohol/barbiturates).Type: GrantFiled: June 2, 1995Date of Patent: January 28, 1997Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Tohru Nakao, Hiroshi Tanaka, Yasuto Morimoto, Shuzo Takehara
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Patent number: 5596106Abstract: This invention discloses methods of using certain aryl-benzo[b]thiophene and benzo[b]furan compounds to block or inhibit cannabinoid receptors in mammals. It also discloses novel compounds which are antagonists of the cannabinoid receptors and also discloses pharmaceutical formulations which contain the compounds as an active ingredient.Type: GrantFiled: June 7, 1995Date of Patent: January 21, 1997Assignee: Eli Lilly and CompanyInventors: George J. Cullinan, Kennan J. Fahey, Gary A. Koppel
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Patent number: 5587486Abstract: 1-amino-2-cyclohexene compounds represented by the following formula (I): ##STR1## wherein the substituents are as defined in the specification, a process for preparing the compounds and their use as intermediates in the production of medicinal and agricultural agents is disclosed.Type: GrantFiled: June 30, 1995Date of Patent: December 24, 1996Assignee: Kuraray Co., Ltd.Inventors: Naoshi Nakagawa, Tadashi Hatanaka, Tatsuhiko Hayashibara, Manzo Shiono
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Patent number: 5567828Abstract: The present invention provides compounds with nitrogen-containing non-basic side chains of formula II ##STR1## wherein R.sup.1 and R.sup.2, independently, are H, OH, O(C.sub.1 -C.sub.6 alkyl), O--C(O)--(C.sub.1 -C.sub.6 alkyl), O--C(O)--O(C.sub.1 -C.sub.6 alkyl), O--C(O)--Ar, O--C(O)--O--Ar, O--SO.sub.2 --(C.sub.4 -C.sub.6 alkyl), chloro, fluoro, or bromo;W is CHOH, C(O), or CH.sub.2 ;Y is (CH.sub.2).sub.n, or CH(C.sub.1 -C.sub.4 alkyl);V is S, 0, or CH.sub.2 CH.sub.2 ;n is 1, 2, or 3; andAr is optionally substituted phenyl.The present invention also provides pharmaceutical compositions containing compounds of formula II, optionally containing estrogen or progestin, and the use of such compounds, alone, or in combination with estrogen or progestin, for alleviating the symptoms of post-menopausal symptoms, particularly osteoporosis, cardiovascular related pathological conditions, and estrogen-dependent cancer.Type: GrantFiled: June 7, 1995Date of Patent: October 22, 1996Assignee: Eli Lilly and CompanyInventor: Jeffrey A. Dodge
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Patent number: 5565488Abstract: The inventive Oxalylamino-benzofuran- and benzothienyl-derivatives are prepared by reacting the appropriate amino substituted benzofuranes and benzothiophenes with oxalic acid derivatives. The inventive compounds are suitable for the prevention and treatment of acute and chronic inflammatory processes, particularly of the airways.Type: GrantFiled: May 23, 1995Date of Patent: October 15, 1996Assignee: Bayer AktiengesellschaftInventors: Gabriele Braunlich, Rudiger Fischer, Mazen Es-Sayed, Rudolf Hanko, Stephen Tudhope, Graham Sturton, Trevor Abram, Wendy J. McDonald-Gibson, Mary F. Fitzgerald
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Patent number: 5554633Abstract: Compounds of formula (I), and salts and prodrugs thereof, wherein Q is optionally substituted phenyl or benzhydryl; X and Y are each H or together form a group=O; Z is O, S or NR.sup.9, where R.sup.9 is H or C.sub.1-6 alkyl; R.sup.1 represents H or C.sub.1-6 alkyl; R.sup.2 represents C.sub.1-6 alkyl substituted by CONR.sup.7 (CH.sub.2).sub.p R.sup.8 (where R.sup.7 is H or C.sub.1-6 alkyl, R.sup.8 is optionally substituted heteroaryl and p is 0, 1, 2, 3, 4, 5 or 6); R.sup.3 represents H, C.sub.1-6 alkyl or C.sub.2-6 alkynyl; R.sup.4 represents H, C.sub.1-6 alkyl or optionally substitute phenyl; R.sup.5 represents optionally substituted phenyl; R.sup.6 is H or C.sub.1-6 alkyl; and q is 0, 1, 2 or 3; are tachykinin antagonists useful in therapy.Type: GrantFiled: January 27, 1995Date of Patent: September 10, 1996Assignee: Merck, Sharp & Dohme, Ltd.Inventor: Martin R. Teall
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Patent number: 5532382Abstract: Provided are compounds of the formula II ##STR1## wherein R.sub.6 and R.sub.7 are independently hydrogen or C.sub.1 -C.sub.6 alkyl;R.sub.5 is naphthyl, substituted nephthyl, or phenyl substituted one to three times with C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkyl, phenyl, or hydroxy; with the proviso that if the phenyl is substituted once with hydroxy, it must be further be substituted once or twice with C.sub.1 -C.sub.6 alkoxy, C.sub.l -C.sub.6 alkyl, phenyl or hydroxy, and pharmaceutically acceptable salts thereof.Type: GrantFiled: March 13, 1995Date of Patent: July 2, 1996Assignee: Eli Lilly and CompanyInventors: Donald G. Carlson, George J. Cullinan, Kennan J. Fahey, William T. Jackson, Neal W. Roehm, Stephen M. Spaethe
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Patent number: 5523416Abstract: The invention provides a process for preparing 6-alkoxy-3-(4-alkoxyphenyl)benzo[B]thiophenes in good yield on a manufacturing scale without generating a thick, potentially yield-reducing, paste. The invention also provides methods for converting a-(-alkoxyphenylthio)-4-alkoxyacetophenones into 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-aminoethoxy)benzoyl]benzo[B]thiophen es via acylation of a dialkoxy benzo[B]thiophene. Each of these preparations relies on an intramolecular cyclization of a dialkoxy acetophenone derivative to yield a benzo[B]thiophene without generating a thick paste that lowers overall yields on a manufacturing scale.Type: GrantFiled: April 14, 1995Date of Patent: June 4, 1996Assignee: Eli Lilly and CompanyInventor: Charles A. Alt
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Patent number: 5512684Abstract: The invention provides a process for preparing 6-alkoxy-3-(4-alkoxyphenyl)benzo B!thiophenes in good yield on a manufacturing scale without generating a thick, potentially yield-reducing, paste. The invention also provides methods for converting a-(-alkoxyphenylthio)-4-alkoxyacetophenones into 6-hydroxy-2-(4-hydroxyphenyl)-3- 4-(2-aminoethoxy)benzoyl!benzo B!thiophen es via acylation of a dialkoxy benzo B!thiophene. Each of these preparations relies on an intramolecular cyclization of a dialkoxy acetophenone derivative to yield a benzo B!thiophene without generating a thick paste that lowers overall yields on a manufacturing scale.Type: GrantFiled: August 8, 1995Date of Patent: April 30, 1996Assignee: Eli Lilly and CompanyInventor: Charles A. Alt
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Patent number: 5508450Abstract: Benzopyran derivatives which have an inhibitory effect on the Maillard reaction as well as an antioxidizing effect are described herein. These derivatives may be utilized in the treatment and/or prevention of diabetic complications such as, for example, coronary heart disease, peripheral circulatory insufficiency or failure, cerebrovascular hindrance, neurogenous diabetes, nephropathy, arteriosclerosis, arthrosclerosis, cataracts and retinopathy. Further, the derivatives may also be used in the treatment and/or prevention of diseases induced by aging and in the treatment and/or prevention of diseases caused by the formation of peroxidized fat.Type: GrantFiled: September 30, 1994Date of Patent: April 16, 1996Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Shuichi Ohuchida, Masaaki Toda, Tsumoru Miyamoto
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Patent number: 5502061Abstract: The present invention provides HIV protease inhibitors, pharmaceutical formulations containing those compounds and methods of treating and/or preventing HIV infection and/or AIDS.Type: GrantFiled: September 26, 1994Date of Patent: March 26, 1996Assignee: Eli Lilly and CompanyInventors: Kwan Y. Hui, Charles D. Jones, Louis N. Jungheim, Pamela A. Pennington
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Patent number: 5498630Abstract: A method of controlling Take-All disease of plants by applying a fungicide of the formula ##STR1## wherein Z1 and Z2 are C and are part of an aromatic ring which is benzothiophene; andA is selected from --C(X)-amine wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical, --C(O)--SR.sub.3, --NH--C(X)R.sub.4, and --C(.dbd.NR.sub.3)--XR.sub.7 ;B is --W.sub.m --Q(R.sub.2).sub.3 or selected from O-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R.sub.4 ;Q is C, Si, Ge, or Sn;W is --C(R.sub.3).sub.p H.sub.(2-p) --; or when Q is C, W is selected from --C(R.sub.3).sub.p H(.sub.2-p), --N(R.sub.3).sub.m H(.sub.1-m)--, --S(O)p--, and --O--;X is 0 or S;n is 0, 1, 2, or 3;m is 0 or 1;p is 0, 1, or 2;each R and R.sub.2 is independently defined herein;R.sub.3 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; andR.sub.7 is C.sub.1 -C.sub.Type: GrantFiled: November 16, 1994Date of Patent: March 12, 1996Assignee: Monsanto CompanyInventors: Dennis P. Phillion, Diane S. Braccolino, Matthew J. Graneto, Wendell G. Phillips, Karey A. Van Sant, Daniel M. Walker, Sai C. Wong
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Patent number: 5491152Abstract: The present invention provides compounds of Formula I, ##STR1## or a pharmaceutically acceptable salt forms thereof, which are inhibitors of acyl-Coenzyme A: cholesterol O-acyltransferase (ACAT), pharmaceutical compositions containing such compounds, processes for the preparation of such compounds, and the use of such compounds as antihypercholesterolemic and/or antiatherosclerotic agents.Type: GrantFiled: March 23, 1994Date of Patent: February 13, 1996Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Richard G. Wilde, Soo S. Ko, Jeffrey T. Billheimer
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Patent number: 5482966Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene or a heteroaryl diradical;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.Type: GrantFiled: June 13, 1994Date of Patent: January 9, 1996Assignees: Zeneca Limited, Zeneca Pharma S.A.Inventors: Thomas G. C. Bird, Patrick Ple
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Patent number: 5472978Abstract: Compounds of formula (I), and salts and prodrugs thereof, wherein Q represents optionally substituted phenyl, naphthyl, indolyl, benzothiophenyl, benzofuranyl, benzyl or indazolyl; Z represents O, S or NR.sup.8 ; X and Y are H or are together .dbd.O; R.sup.1 and R.sup.2 are H; optionally substituted C.sub.1-6 alkyl; optionally substituted phenyl(C.sub.1-4 alkyl); COR.sup.c ; CO.sub.2 R.sup.c ; CONR.sup.c R.sup.d ; CONR.sup.c COOR.sup.d ; or SO.sub.2 R.sup.c ; R.sup.3 is H or C.sub.1-6 alkyl, R.sup.4 is H , C.sub.1-6 alkyl or optionally substituted phenyl; and R.sup.5 represents optionally substituted phenyl; are tachykinin antagonists. They and compositions thereof are useful in therapy.Type: GrantFiled: December 10, 1993Date of Patent: December 5, 1995Assignee: Merck Sharp & Dohme Ltd.Inventors: Raymond Baker, Angus M. MacLeod, Kevin J. Merchant, Christopher J. Swain
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Patent number: 5470999Abstract: Compounds of Formula 1 ##STR1## where R.sub.1 -R.sub.5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.Type: GrantFiled: December 30, 1993Date of Patent: November 28, 1995Assignee: Allergan, Inc.Inventor: Roshantha A. Chandraratna
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Patent number: 5464863Abstract: An N-heteroaryl-N'-phenylurea derivative represented by the general formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are as defined in the description of the specification which is useful as a prophylactic and therapeutic agent for hypercholesterolemia, atherosclerosis and diseases caused by them.Type: GrantFiled: September 24, 1994Date of Patent: November 7, 1995Assignee: Nihon Nohyaku Co., Ltd.Inventors: Masashi Nagamine, Kenji Yamamoto, Yoshimitsu Matsui, Kenji Horiuchi, Masanori Yoshida
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Patent number: 5451605Abstract: Compounds of the formula ##STR1## where R.sub.1 -R.sub.5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.Type: GrantFiled: December 30, 1993Date of Patent: September 19, 1995Assignee: Allergan, Inc.Inventors: Roshantha A. Chandraratna, Richard L. Beard
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Patent number: 5441984Abstract: The present invention provides novel urea, thiourea and guanidine derivatives, pharmaceutical formulations thereof and a method of using same to prevent diabetic complications.Type: GrantFiled: November 14, 1994Date of Patent: August 15, 1995Assignee: Eli Lilly and CompanyInventors: William F. Heath, Jr., Jill A. Panetta, John K. Shadle
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Patent number: 5440035Abstract: The invention concerns novel, pharmaceutically useful, amide derivatives of certain benzoheterocyclylalkanoic acids (and related tetrazoles and acylsulphonamides) of the formula I and salts thereof, wherein the radicals R.sup.1, R.sup.2, L, X, Y, Z, A.sup.1, Q, A.sup.2 and M have the meanings set out in the specification. The invention also includes pharmaceutical compositions incorporating a formula I compound or a salt thereof, a process for the manufacture of the said compound, together with intermediates for use in the latter process.Type: GrantFiled: October 25, 1994Date of Patent: August 8, 1995Assignee: Zeneca Inc.Inventors: Peter R. Bernstein, Frederick J. Brown, Victor G. Matassa, Ying K. Yee
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Patent number: 5426191Abstract: An improved process for the preparation of 3-chlorobenzo[b]thiophene-2-carbonyl chlorides is described where a cinnamic acid is converted in the presence of thionyl chloride and a 4-N,N'-disubstituted aminopyridine in one step to the desired product.Type: GrantFiled: December 3, 1993Date of Patent: June 20, 1995Assignee: Warner-Lambert CompanyInventor: Jonathan Walker
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Patent number: 5424455Abstract: A heterocyclic compound of the formula, ##STR1## wherein A and B are each hydrogen, halogen, alkyl or alkoxy, R.sup.1 is alkylene having upto 6 carbon atoms, X is direct linkage or divalent group such as --O--, --S--and the like, T and U are each hydrogen or alkyl, l is 0 or 1 to 3, Q is 5-, 6- or 7- membered saturated or unsaturated heterocyclic residue, and Y is hydrogen, halogen, alkyl, alkoxy or ##STR2## and B are taken together with each other to form methylene-dioxy, which is useful for dyeing or printing hydrophobic fiber materials with superior dyeability to give a dyed or printed product of a red color excellent in fastness properties, particularly those such as washing fastness.Type: GrantFiled: July 28, 1993Date of Patent: June 13, 1995Assignee: Sumitomo Chemical Co., Ltd.Inventors: Jun Yamamoto, Yasuyoshi Ueda, Junichi Sekihachi, Yosuke Yamamoto, Takashi Omura
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Patent number: 5422335Abstract: A herbicidal composition containing one or more substituted 2-aminothiophenes of the formula I ##STR1## where R.sup.1 and R.sup.2 together from a C.sub.4 -alkylene chain to which a benzene ring may be fused,R.sup.3 is --CN or CX--R.sup.6, where R.sup.6 is hydroxyl, C.sub.1 -C.sub.4 -alkoxy or amino,R.sup.4 is hydrogen or a phenyl group which may carry one or two nitro radicals,--PO(OR.sup.8).sub.2, --CX--R.sup.9, --SO.sub.2 R.sup.10, --CX--N(H) --CO--R.sup.8 or --CX--N(R.sup.7)--SO.sub.2 --R.sup.11,whereR.sup.8 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl groupR.sup.9 is C.sub.1 -C.sub.20 -alkyl, partially or completely halogenated C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.6 -cycloalkyl, or amino, C.sub.1 -C.sub.4 -alkylamino, C.sub.3 -C.sub.8 -cycloalkylamino, phenyl or phenylamino, where the aromatic moiety may carry at least one of nitro and halogen;R.sup.10 is C.sub.1 -C.sub.4 -alkyl or phenyl, which may carry one C.sub.1 -C.sub.4 -alkyl radical;R.sup.Type: GrantFiled: June 7, 1993Date of Patent: June 6, 1995Assignee: BASF AktiengesellschaftInventors: Helmut Hagen, Gerhard Nilz, Helmut Walter, Andreas Landes
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Patent number: 5403939Abstract: A process for production of 2-acetylbenzo[b]thiophene represented by the formula (I): ##STR1## comprising the steps of: (1) reacting 2-halogenobenzaldehyde represented by the formula (II): ##STR2## wherein X represents a halogen atom, with a compound represented by the formula (III):H.sub.i S.sub.j M.sub.kwherein M represents an alkali metal, i represents zero or 1, j represents an integer of at least 1, and k represents an integer of 1 or 2, and preferably also with sulfur; and(2) reacting the reaction product with a monohalogenoacetone represented by the formula (IV) ##STR3## wherein X.sup.1 represents a halogen atom.Type: GrantFiled: September 9, 1993Date of Patent: April 4, 1995Assignee: Takeda Chemical Industries, Ltd.Inventors: Naoto Yazawa, Yoshinori Saito, Hidetaka Hiyoshi
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Patent number: 5385931Abstract: The invention relates to new sulphonamide derivatives of benzo-cyclic or benzo-heterocyclic acids and their derivatives of general formula I ##STR1## in which: R represents a straight-chain or branched lower alkyl radical having 1 to 9 C;a phenyl radical which is unsubstituted or substituted by one or more groups:straight-chain or branched lower alkyl having 1 to 4 C, halogeno, alkoxy, nitro, amino, dialkylamino or CF.sub.3 ;a substituted or unsubstituted naphthalene;a thiophenyl radical;R.sub.1 represents a hydrogen or a straight-chain or branched lower alkyl or a benzyl;R.sub.2 represents a hydrogen, a straight-chain or branched lower alkyl group, a substituted or unsubstituted phenyl group or an aralkyl group;R.sub.3 represents a hydrogen or a straight-chain or branched lower alkyl (1 to 6 C);--X-- represents a divalent functional radical chosen from the following: --CH.sub.2 --; ##STR2## where R.sub.Type: GrantFiled: December 28, 1990Date of Patent: January 31, 1995Assignee: Pierre Fabre MedicamentInventors: Dennis Bigg, Alain Duflos, Jean-Pierre Rieu
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Patent number: 5380748Abstract: A trialkylamine derivative represented by the formula (1) or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different from each other and each represents lower alkyl;R.sup.3, R.sup.4 and R.sup.5 may be the same or different from one another and each represents hydrogen, lower alkyl, lower alkoxy, lower alkoxycarbonyl or halogen;R.sup.6 and R.sup.7 may be the same or different from each other and each represents hydrogen or lower alkyl;R.sup.8 represents hydrogen, lower alkyl, lower alkoxy or halogen;X represents oxygen, sulfur, --CH.dbd.N-- or --CH.dbd.CH--;Y represents oxygen, sulfur, methylene, N--R.sup.11 (wherein R.sup.11 represents lower alkyl), SO or SO.sub.2 ;Z represents --OCO(CH.sub.2).sub.p .about. or --OCH.sub.2 (CH.sub.2).sub.p .about. (wherein p represents a number of 0 to 4 and symbol .about.Type: GrantFiled: August 30, 1993Date of Patent: January 10, 1995Assignee: Zeria Pharmaceutical Co., Ltd.Inventors: Yoshiaki Muto, Hiromi Ichikawa, Kuniyoshi Ogura, Kyoji Chaki, Masao Seiki, Toshihiko Takemasa