Having -c(=x)-, Wherein X Is Chalcogen, Attached Indirectly To Ring Carbon Of The Five-membered Hetero Ring By An Acyclic Carbon Or Acyclic Carbon Chain (e.g., Indole-3-acetic Acid, Etc.) Patents (Class 548/494)
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Patent number: 5330981Abstract: This application describes 3-arylalkyl esters of 4,5-dihydro-9,10-dioxo-2-anthracenecarboxylic acid and a process for making them. Also described is a method of using the compounds in the treatment of arthritis.Type: GrantFiled: December 30, 1992Date of Patent: July 19, 1994Assignee: Istituto Gentili S.p.A.Inventors: Sergio Rosini, Maurizio Mian
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Patent number: 5326759Abstract: Novel 9-amino-7-(substituted amino)-6-demethyl-6-deoxytetracyclines having activity against a wide spectrum of organisms including organisms which are resistant to tetracyclines are disclosed. Also disclosed are intermediates and methods for making the novel compounds of the present invention.Type: GrantFiled: November 1, 1993Date of Patent: July 5, 1994Assignee: American Cyanamid CompanyInventors: Joseph J. Hlavka, Phaik-Eng Sum, Yakov Gluzman, Ving J. Lee
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Patent number: 5322951Abstract: An intermediate compound of Formula (V): ##STR1## wherein G is COQ.sub.1 and Q.sub.1 represents chloro, bromo, C.sub.1-4 alkoxy, PhO--, Cl.sub.5 C.sub.6 O--, Cl.sub.3 CO--, succinimidyloxy or imidazolyloxy; the remainder of the terms R.sub.1, R.sub.2, R.sub.3, R.sub.4, X and Y are defined in the specification. The intermediates of Formula V are useful for preparing 1-(2,3-dihydro-1-carboxamide final products wherein said final products possess 5-HT M-receptor antagonist activity.Type: GrantFiled: November 13, 1992Date of Patent: June 21, 1994Assignee: Beecham Group, p.l.c.Inventors: Francis D. King, Karen A. Joiner
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Patent number: 5312928Abstract: A substantially pure compound of the formula: ##STR1## wherein each of R.sub.1 and R.sub.2, independently, is H, CH.sub.3, CF.sub.3, F, Cl, Br, I, OH, OCH.sub.3, OCF.sub.3, SH, SCH.sub.3, NH.sub.2, N.sub.3, NO.sub.2, CN, COOH, CONH.sub.2, CH.sub.2 CONH.sub.2, or SO.sub.2 NH.sub.2 ;R.sub.3 is H, CH.sub.3, COOH, CONH.sub.2, or COOR where R is C.sub.1-4 alkyl;each R.sub.4, independently, is H or C.sub.1-6 alkyl;X is CH.sub.2, CH.sub.2 CH.sub.2, CH.dbd.CH, or CH.sub.2 CH.sub.2 CH.sub.2 ; ##STR2## each Z, independently, is H, CH.sub.3, or Q where Q is a hydrophobic acyl, benzoyl, phenacetyl, benzyloxycarbonyl, alkoxycarbonyl, or N-methyl-dihydropyridine-3-carbonyl linked to N by an amide bond which is cleavable by an endogenous central nervous system enzyme;D is H or ##STR3## where R.sub.5 is H or C.sub.Type: GrantFiled: February 11, 1991Date of Patent: May 17, 1994Assignee: Cambridge NeuroscienceInventors: Stanley M. Goldin, Kazumi Kobayashi, Andrew G. Knapp, Lee Margolin, Subbarao Katragadda, Deborah Daly, Lain-Yen Hu, N. Laxma Reddy
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Patent number: 5296519Abstract: Disclosed is a novel UV light absorbing compound which can preferably be employed in the art of colored molding plastics, resin films, heat-sensitive transfer materials, liquid crystal display materials, color photographs and the like, and method for producing thereof. The UV light absorbing compound is characterized by the general formula: ##STR1## wherein R.sup.1 represents linear or branched alkyl or aralkyl group, and R.sup.2 represents --CN or --COOR.sup.3, wherein R.sup.3 represents substituted or unsubstituted alkyl or aralkyl group.Type: GrantFiled: June 11, 1992Date of Patent: March 22, 1994Assignee: Orient Chemical Industries, Ltd.Inventor: Masahiro Otsuka
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Patent number: 5292883Abstract: A compound of the formula ##STR1## wherein R.sup.1 is hydrogen, loweralkyl, phenyl, phenyl substituted by one or more loweralkyl, loweralkoxy, halogen, or trifluoromethyl groups, phenylloweralkyl or phenylloweralkyl in which the phenyl group is substituted by one or more loweralkyl, loweralkoxy, halogen, or trifluoromethyl groups; R.sup.2 is loweralkyl, furanylloweralkyl, thienylloweralkyl, pyrrolylloweralkyl, pyridinylloweralkyl, phenylloweralkyl, or phenylloweralkyl in which the phenyl group is substituted by one or more loweralkyl, loweralkoxy, halogen, or trifluoromethyl groups; X is hydrogen, loweralkyl, loweralkoxy, halogen, or trifluoromethyl; m is 0, 1 or 2; n is 1 or 2; an optical isomer thereof or a salt thereof.Type: GrantFiled: May 27, 1993Date of Patent: March 8, 1994Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Lawrence L. Martin, Denise M. Flanagan, Joseph F. Payack
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Patent number: 5290946Abstract: A process for synthesizing compounds of the formula ##STR1## utilizing, as intermediates, oxalyl chloride or bromide and compounds of the formulae R.sub.1 R.sub.2 N--CHO and CH.sub.2 .dbd.CH--O--R.sub.10 are processes for synthesizing compounds of the formula ##STR2## utilizing, as intermediates, compounds of Formula I wherein R.sub.1 is phenyl or substituted phenyl or intermediates in the synthesis of the compounds of formula I which intermediates have the formula ##STR3## wherein R.sub.1 is C.sub.1-3 alkyl, phenyl or phenyl substituted by 1 to 3 substituents each of which is independently C.sub.1-3 alkyl, C.sub.1-3 alkoxy, fluoro, chloro, bromo or nitro (maximum of two nitro groups),R.sub.2 is C.sub.1-3 alkyl,R.sub.10 is C.sub.1-6 alkyl,X.sup..crclbar. is chloride or bromide, andR.sub.3 -R.sub.6 are as defined in the specification.Type: GrantFiled: November 23, 1992Date of Patent: March 1, 1994Assignee: Sandoz Ltd.Inventors: George T. Lee, Prasad K. Kapa, Oljan Repic
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Patent number: 5283251Abstract: Indole derivatives of the following formula: ##STR1## wherein R.sup.1 is carboxy(lower)alkyl or protected carboxy(lower)alkyl,R.sup.2 is hydrogen, lower alkyl or halogen,R.sup.3 and R.sup.4 are each hydrogen or lower alkyl,R.sup.5 is ar(lower)alkyl which may have suitable substituent(s), andA is carbonyl, sulfonyl or lower alkylene, or a pharmaceutically acceptable salt thereof, which are useful as a testosterone 5.alpha.-reductase inhibitor.Type: GrantFiled: October 8, 1992Date of Patent: February 1, 1994Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Satoshi Okada, Kozo Sawada, Natsuko Kayakiri, Yuki Saitoh, Hirokazu Tanaka, Masashi Hashimoto
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Patent number: 5240956Abstract: 2-Heteroaromatic alkanoate esters which are useful as inhibitors of human leukocyate or neutrophil elastase.Type: GrantFiled: April 13, 1992Date of Patent: August 31, 1993Assignee: Cortech, Inc.Inventors: Gary P. Kirschenheuter, Raymond T. Cunningham, John C. Cheronis
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Patent number: 5239083Abstract: The present invention provides Indole derivatives represented by the formula (I) ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently represent hydrogen or lower alkyl;R.sup.4 represents hydrogen, lower alkyl or cycloalkyl;R.sup.5 represents hydrogen, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl,--CHR.sup.7 R.sup.8 where R.sup.7 and R.sup.8 independently represent hydrogen, alkyl, alkenyl, alkynyl, substituted or unsubstituted cycloalkyl, --(CH.sub.2).sub.m OR.sup.9 (wherein m is an integer of 1-3 and R.sup.9 is lower alkyl), substituted or unsubstituted aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted furyl, or substituted or unsubstituted thienyl], ##STR2## (wherein Y is CH.sub.2, O, S, CH.sub.2 --CH.sub.2, CH.dbd.CH, CH.sub.2 --O or CH.sub.2 --S); R.sup.Type: GrantFiled: March 10, 1992Date of Patent: August 24, 1993Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Toshiaki Kumazawa, Hitoshi Takami, Hiroyuki Obase, Nobuyuki Kishibayashi, Akio Ishii
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Patent number: 5229413Abstract: Compositions containing certain indole-2-carboxylate compounds and derivatives are described as being therapeutically effective in treatment of CNS disorders resulting from neurotoxic damage or neurodegenerative diseases, particularly those CNS disorders resulting from ischemic events. Preferred compounds are of the formula ##STR1## wherein each of R.sup.5 and R.sup.6 is independently selected from hydrido, bromo, chloro and fluoro, and wherein each of R.sup.10 and R.sup.12 is independently selected from hydrido and lower alkyl, and pharmaceutically-acceptable salts thereof.Type: GrantFiled: February 3, 1992Date of Patent: July 20, 1993Assignee: G. D. Searle & Co.Inventors: Nancy M. Gray, Brian K. Cheng, William F. Hood, Michael S. Dappen, Alex A. Cordi
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Patent number: 5212320Abstract: Indole derivatives of the formula ##STR1## and pharmaceutical compositions thereof. They are useful for treating or preventing testosterone 5-alpha-reductase-mediated diseases, such as alopecia, acnes and prostatism.Type: GrantFiled: September 11, 1991Date of Patent: May 18, 1993Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Satoshi Okada, Kozo Sawada, Natsuko Kayakiri, Yuki Saitoh, Hirokazu Tanaka, Masashi Hashimoto
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Patent number: 5210215Abstract: 3-indolepyruvic acid derivatives substituted on the benzene moiety show good antagonizing activity on excitatory aminoacids and on free radicals, for which reason they are therapeutic agents in cerebral and peripheral degenerative pathologies. Their method of production by passage through the corresponding substituted triptophane.Type: GrantFiled: September 18, 1990Date of Patent: May 11, 1993Assignee: Polifarma S.p.A.Inventors: Vincenzo Politi, Giovanna De Luca, Giovanni Di Stazio, Mario Materazzi
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Patent number: 5206382Abstract: A compound having the formula: ##STR1## wherein R.sub.1 and R.sub.2 independently is selected from the group consisting of H, C.sub.3 -C.sub.12 straight or branched alkyl, aryl or lower alkyl-substituted aryl; or R.sub.1 and R.sub.2 may be joined to form a 4-to 6-membered saturated or unsaturated ring or a 4-to 6-membered saturated or unsaturated lower alkyl-substituted ring; R.sub.3 is H, C.sub.1 -C.sub.12 straight or branched alkyl, NO.sub.2, NH.sub.2, N.sub.3, CN, halogen, CO.sub.2 R, OR, or SR wherein R is H or lower alkyl; R.sub.4 is H, C.sub.1 -C.sub.12 straight or branched alkyl, NO.sub.2, NH.sub.2, N.sub.3, CN, halogen, CO.sub.2 R, OR, or SR wherein R is H or lower alkyl; A is nothing or a C.sub.1 -C.sub.5 alkylene to form a ring; Z is 0, NH, S or --CH.dbd.CH--; and n is an integer of 1-3; or a pharmaceutically acceptable salt thereof. The compounds are useful in compositions and methods for treating psychiatric and neurological disorders.Type: GrantFiled: June 27, 1991Date of Patent: April 27, 1993Assignee: Fidia Georgetown Institute for the NeurosciencesInventors: Erminio Costa, Alessandro Guidotti, Alan Kozikowski, Dawei Ma
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Patent number: 5204337Abstract: Novel compounds for the inhibition of sex steroid activity for the treatment of both androgen-related and estrogen-related diseases include for example 15- and 16-halo substituted compounds such as: ##STR1## The compounds are characterized by an estrogenic nucleus substituted with a substituent of the formula --R.sup.1 [B--R.sup.2 --].sub.x L--G whereinat least one of L and G is a polar moiety distanced from a ring carbon of the estrogenic nucleus by a least three intervening atoms:x is an integer from 0-6;R.sup.1 and R.sup.2 are independently either absent or selected from the group consisting of straight- or branched-chain alkylene, straight- or branched-chain alkynylene, straight- or branched-chain alkenylene, phenylene, and fluoro-substituted analogs of the foregoing; andB is either absent or selected from the group consisting of --O--, --Se--, --SO--, --SO.sub.2 --, --NR.sup.3 --, --SiR.sup.3.sub.2, --CR.sup.3 OR.sup.3 --, NR.sup.3 CO--, NR.sup.3 CS--, --CONR.sup.3 --, CSNR.sup.Type: GrantFiled: July 21, 1992Date of Patent: April 20, 1993Assignee: Endorecherche Inc.Inventors: Fernand Labrie, Yves Merand
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Patent number: 5190968Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.Type: GrantFiled: September 30, 1991Date of Patent: March 2, 1993Assignee: Merck Frosst Canada, Inc.Inventors: John W. Gillard, John H. Hutchinson
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Patent number: 5189178Abstract: Compounds of the formulas ##STR1## wherein each R.sup.1 is independently H or alkyl (1-8C) and R.sup.2 is alkyl (1-8C) or wherein the proximal R.sup.1 and R.sup.2 taken together are --(CH.sub.2).sub.p -- wherein p=3-5;R.sup.3 is H or alkyl (1-4C);R.sup.4 is fused or conjugated unsubstituted or substituted bicycloaryl methylene;n is 0, 1 or 2;m is 0 or 1; andX is OR.sup.5 or NHR.sup.5, wherein R.sup.5 is H or substituted or unsubstituted alkyl (1-12C), aryl (6-12C), aryl alkyl (6-16C); orX is an amino acid residue or amide thereof; orX is the residue of a cyclic amine or heterocyclic amine;wherein R.sup.6 is H or lower alkyl (1-4C) and R.sup.7 is H, lower alkyl (1-4C) or an acyl group, and wherein --CONR.sup.3 -- is optionally in modified isosteric formare useful for treating conditions which are characterized by unwanted matrix metalloprotease activities.Type: GrantFiled: August 20, 1991Date of Patent: February 23, 1993Inventors: Richard E. Galardy, Damian Grobelny
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Patent number: 5166170Abstract: There are disclosed various compounds depicted by the general formula, ##STR1## where the parameters X, Y, R.sub.1, R.sub.2, and R.sub.3 are as defined in the specification. These compounds are disclosed as topical antiinflammatory agents useful for the treatment of various skin disorders including exogenous dermatitis, endogenous dermatitis, dermatitis of unknown etiology and other cutaneous disorders with an inflammatory component.Type: GrantFiled: July 3, 1989Date of Patent: November 24, 1992Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: John J. Tegeler, Eileen M. Gardenhire, Grover C. Helsley
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Patent number: 5143536Abstract: A rooting composition is set forth comprising a water swellable gel containing auxin in an amount effective to stimulate root growth, the gel comprising a high molecular weight organic acid, ketone or ester or combinations thereof. Root formation of a cutting is stimulated by planting the cutting in the soil with the aformentioned rooting composition adhered to the portion of the cutting proximal where it was cut from a living plant. The auxins are maintained close to the cutting whereby they are highly effective and the gel serves as an artificial root to bring water and nutrients to the cutting as it develops its own root system.Type: GrantFiled: October 5, 1987Date of Patent: September 1, 1992Inventor: Walter H. Runkis
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Patent number: 5132319Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.Type: GrantFiled: March 28, 1991Date of Patent: July 21, 1992Assignee: Merck Frosst Canada, Inc.Inventors: Yves Girard, Pierre Hamel, Daniel Delorme, Rejean Fortin
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Patent number: 5128482Abstract: The invention provides a process for the production of 3-(1-amino-1,3-dicarboxy-3-hydroxy-but-4-yl) indole and certain salts and internal condensation products thereof. An unsaturated indolyl ester is reacted with ethylchloro(hydroxyimino)acetate in the presence of triethylamine in an organic solvent to cause a 1,3-dipolar addition reaction to form a di-ester. The di-ester is saponified to form a di-acid which di-acid is then reduced to form either the product indole or a salt thereof.Type: GrantFiled: January 18, 1991Date of Patent: July 7, 1992Assignee: Technology Finance Corporation (Proprietary) LimitedInventors: Johan Olivier, Karl Bischofberger
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Patent number: 5118853Abstract: Process for the synthesis of compounds of the formula ##STR1## comprising the steps of (i) reacting a compound of the formula ##STR2## with oxalyl chloride or oxalyl bromide to form the corresponding compound of the formula ##STR3## (ii) reacting said compound of the formula ##STR4## with a compound of the formula ##STR5## to form the corresponding compound of the formula ##STR6## (iii) hydrolyzing said compound of the formula ##STR7## to obtain the corresponding compound of the formula ##STR8## the use of the compounds of the formula ##STR9## for the synthesis of the compounds of the formula ##STR10## and the use of the intermediates of Formula VII for the direct synthesis of the compounds of Formula II,whereinR.sub.1 is C.sub.1-3 alkyl, phenyl or phenyl substituted by 1 to 3 substituents each of which is independently C.sub.1-3 alkyl, C.sub.1-3 alkoxy, fluoro, chloro, bromo or nitro (maximum of two nitro groups),R.sub.Type: GrantFiled: February 26, 1991Date of Patent: June 2, 1992Assignee: Sandoz Ltd.Inventors: George T. Lee, Oljan Repic
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Patent number: 5118700Abstract: Indole derivative for leukotriene antagonists of the formula ##STR1## wherein groups A, B, D, E, F & G are as described in the specification.Type: GrantFiled: July 2, 1990Date of Patent: June 2, 1992Assignee: Bayer AktiengesellschaftInventors: John E. Butler, Nigel J. Cuthbert
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Patent number: 5114962Abstract: New amino acid esters, a process for their preparation, medicaments containing them, and the use thereof The invention relates to amino acid esters of the formula I ##STR1## in which n is 1 or 2, R, R.sup.1, R.sup.2 and R.sup.3 denote hydrogen or a defined radical, R.sup.4 together with R.sup.5 and the atoms carrying them form a heterocyclic ring system, to a process for their preparation, to agents containing them, and to the use thereof.Type: GrantFiled: June 19, 1990Date of Patent: May 19, 1992Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Ruger, Hansjorg Urbach, Reinhard Becker, Franz Hock
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Patent number: 5106990Abstract: The present invention relates to a dye represented by formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, each represents a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkyl group having a substituent selected from the group consisting of a sulfonic group, carboxyl group and hydroxyl group, and Z.sup.1 and Z.sup.2 each represents a group of non-metallic atoms necessary for the formation of a benzo-condensed of naphtho-condensed ring, or a benzo-condensed or naphtho-condensed ring having a substituent selected from the group consisting of a sulfonic group, a carboxyl group, an hydroxyl group, a halogen atom, a cyano group, an amino group and a C.sub.1 -C.sub.5 alkyl group connected to the ring directly or through a divalent connection group, with a proviso that R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, Z.sup.1 and Z.sup.Type: GrantFiled: March 28, 1989Date of Patent: April 21, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Shigeru Ohno, Yuji Mihara, Keiichi Adachi
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Patent number: 5095031Abstract: Substituted indolyl compounds of the formula ##STR1## are potent inhibitors of the lipoxygenase enzymes and are useful as agents for the treatment of allergies and inflammatory disease states.Type: GrantFiled: August 20, 1990Date of Patent: March 10, 1992Assignee: Abbott LaboratoriesInventors: Dee W. Brooks, George W. Carter, Joseph F. Dellaria, Robert G. Maki, Karen E. Rodriques
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Patent number: 5081145Abstract: Indole-2-alkanoic acids are disclosed. The compounds act as prostaglandin and thromboxane antagonists and are useful in treating asthma, inflammation, diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion and dismenorrhea and as cytoprotective agents.Type: GrantFiled: February 1, 1990Date of Patent: January 14, 1992Assignee: Merck Frosst Canada, Inc.Inventors: Yvan Guindon, John W. Gillard, Christiane Yoakim, Thomas R. Jones, Rejean Fortin
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Patent number: 5070208Abstract: Optically active tryptophan is crystallized by a modification of a method of crystrallization of optically active tryptophan through neutralization by mixing an acidic or alkaline aqueous solution of optically active tryptophan, which is obtained by the removal of impurities from an acidic or alkaline aqueous solution of optically active tryptophan containing impurities which inhibit flocculation and crystallization of optically active tryptophan, with an alkali or an acid, by combining portions of an alkali or acid with portions of an acidic or alkaline aqueous solution of optically active tryptophan, from which the impurities have been removed, thereby neutralizing the aqueous solution containing optically active tryptophan such that the pH of the solution to be crystallized is kept in a range of 3 to 8, and simultaneously crystallizing optically active tryptophan as flocculated crystals.Type: GrantFiled: March 15, 1991Date of Patent: December 3, 1991Assignee: Ajinomoto Company, Inc.Inventors: Kenichi Yarita, Takahisa Tada, Ryuichiro Kasatani
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Patent number: 5064853Abstract: All possible isomeric forms and mixtures thereof of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of indolyl, pyridyl, piperidinyl, quinolyl, thiazolyl and aryl of 6 to 14 carbon atoms and aralkyl of 7 to 18 carbon atoms with the latter two being unsubstituted or substituted with at least one member of the group consisting of halogen, alkyl and alkoxy of 1 to 8 carbon atoms, dialkylamino with alkyls of 1 to 8 carbon atoms, --CF.sub.3, --CN and --NO.sub.2, R.sub.2 is selected from the group consisting of ##STR2## Ar' are selected from the group consisting of pyridyl, indolyl, thiazolyl and aryl of 6 to 14 carbon atoms with the latter and the phenyl ring of b) being substituted or substrituted with at least one member of the group consisting of halogen, alkyl and alkoxy of 1 to 8 carbon atoms, dialkylamino with alkyls of 1 to 8 carbon atoms, --CF.sub.3, --CN and --NO.sub.2 and R.sub.3 is hydrogen or R.sub.2 and R.sub.Type: GrantFiled: February 12, 1990Date of Patent: November 12, 1991Assignee: Roussel UclafInventors: Jean-Claude Gasc, Daniel Humbert, Mario Vekens
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Patent number: 5051442Abstract: The present invention is directed to a new class of 3-indolyl thioacetate derivatives which the NMDA antagonists.Type: GrantFiled: April 25, 1990Date of Patent: September 24, 1991Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Francesco G. Salituro, Bruce M. Baron
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Patent number: 5049679Abstract: This invention provides a series of novel heterocyclic amides of formula I in which the group >X--Y--Z< is selected from >C.dbd.CH--N<, >C.dbd.N--N<, >N--(CH.sub.2)--N<, >CH--CH.sub.2 --N< and <N--N.dbd.C< and the other radicals have the meanings defined in the following specification.The compounds of formula I are leukotriene antagonists. The invention also provides pharmaceutically acceptable salts of the formula I compounds; pharmaceutical compositions containing the formula I compounds, or their salts, for use in the treatment of, for example, allergic or inflammatory diseases, or endotoxic or traumatic shock conditions; and processes for the manufacture of the formula I compounds, as well as intermediates for use in such manufacture.Type: GrantFiled: December 29, 1989Date of Patent: September 17, 1991Assignee: ICI Americas Inc.Inventor: Peter R. Bernstein
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Patent number: 5047555Abstract: There are disclosed a 4-aminophenol derivative of the formula: ##STR1## (wherein R.sup.1 and R.sup.2 each represent a lower alkyl group, Y represents a single bonding arm, a lower alkylene group or a lower alkenylene group, R.sup.3 represents a thienyl group or pyrrolyl group which may be also substituted with a lower alkyl group; benzothienyl group, indolyl group; or a phenol group which is substituted with 1 to 2 groups selected from a lower alkoxy group and a lower alkanoyloxy group; or Y-R.sup.3 represents integrally an alkyl group with 6 to 9 carbon atoms; or a hydrocarbon group with 5 to 14 carbon atoms having 2 or 3 double bonds) or a pharmacologically acceptable salt thereof, and processes for preparing the same.Type: GrantFiled: December 4, 1989Date of Patent: September 10, 1991Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Hirozumi Inoue, Kei Tsuzurahara, Katsuo Ikezawa, Tomofumi Uchida
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Patent number: 5026909Abstract: A method according to the invention comprises mixing the starting biologically active organic compound, an inorganic vehicle and a catalyst in the form of a platinum-group metal, followed by reacting the resulting mixture with an isotope of hydrogen at a temperature of 373-523 K. and cooling the reaction mixture to a temperature of 288-303 K. and isolation of the desired product therefrom. The invention can be useful, for example, in medical and biological studies.Type: GrantFiled: March 22, 1989Date of Patent: June 25, 1991Inventors: Jury A. Zolotarev, Dmitry A. Zaitsev, Vadim J. Tatur, Nikolai F. Myasoedov
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Patent number: 5017583Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are leukotriene antagonists. These compounds inhibit SRS-A and leukotriene synthesis and are antagonists of SRS-A and are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: February 23, 1988Date of Patent: May 21, 1991Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
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Patent number: 5015657Abstract: Inhibiting platelet aggregation and antagonizing thromboxane A.sub.2 with new 2-halogen-substituted N-indolyethyl-sulphonamides of the formula ##STR1## in which R.sup.1 represents hydrogen, halogen, trifluoromethyl, carboxyl or alkoxycarbonyl having up to 8 carbon atoms, orrepresents straight-chain or branched alkyl having up to 8 carbon atoms, or represents cycloalkyl having 3 to 8 carbon atoms, which is optionally substituted by carboxyl, halogen, alkoxy or alkoxycarbonyl having in each case up to 8 carbon atoms, cyano or hydroxyl, orrepresents a group of the formula --S(O).sub.n --R.sup.5,--NR.sup.6 R.sup.7 or --OR.sup.Type: GrantFiled: November 15, 1989Date of Patent: May 14, 1991Assignee: Bayer AktiengesellschaftInventors: Horst Boshagen, Elisabeth Perzborn, Volker-Bernd Fiedler
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Patent number: 5013854Abstract: An improved process for preparing trialkylsilyl ester and acid halide derivatives of carboxylic acids is provided along with novel trialkylsilyl ester intermediates of 2-(2-furyl)-2-methoximinoacetic acid.Type: GrantFiled: February 2, 1989Date of Patent: May 7, 1991Assignee: Eli Lilly and CompanyInventor: Charles A. Bunnell
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Patent number: 5002963Abstract: The present invention is directed to 3-indolepyruvic acid derivatives, compositions and methods of treating central nervous system disturbances due to the presence of an excessive amount of excitatory amino acids.Type: GrantFiled: February 3, 1989Date of Patent: March 26, 1991Inventors: Giovanna De Luca, Giovanni Di Stazio, Andrea Margonelli, Mario Materazzi, Vincenzo Politi
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Patent number: 4997845Abstract: .beta.-Alkylmelatonins are useful as ovulation inhibitors.Type: GrantFiled: May 10, 1990Date of Patent: March 5, 1991Assignee: Eli Lilly and CompanyInventor: Michael E. Flaugh
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Patent number: 4980096Abstract: Surfactants which are blocked against surfactant action (identified herein as "photolabile blocked surfactants") by a photolabile protective or masking group but which, on exposure to actinic radiation, become unblocked are provided. Coating compositions in which surfactant is formed on irradiation are provided by blending the photolabile blocked surfactant with polymeric film-forming materials.Compositions containing the photolabile blocked surfactants are useful when employed as protective coatings on various substrates or as the adhesive in a pressure sensitive adhesive tape. Although initially well adhering to a substrate, such compositions may be readily removed from the substrate following exposure of the same to suitable radiation which unblocks the surfactant to permit it to regain its surfactant activity.Type: GrantFiled: January 15, 1988Date of Patent: December 25, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Gilbert L. Eian, John E. Trend
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Patent number: 4923864Abstract: Simple amides and derivatives thereof useful for inhibiting the angiotensinogen-cleaving action of the enzyme renin.Type: GrantFiled: October 24, 1988Date of Patent: May 8, 1990Assignee: Pfizer Inc.Inventor: Robert L. Rosati
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Patent number: 4918196Abstract: A process for optically isomerizing an optically active alpha-amino acid amide comprising heating a D-alpha-amino acid amide or an L-alpha-amino acid amide in the presence of a strongly basic compound; and a process for producing an L-alpha-amino acid, which comprises(1) subjecting a D,L-alpha-amino acid amide or a mixture of a major amount of a D-alpha-amino acid amide and a minor amount of an L-alpha-amino acid amide to the action of a microorganism having the ability to hydrolyze the L-alpha-amino acid to obtain a hydrolyzate containing the L-alpha-amino acid and D-alpha-amino acid,(2) separating the L-alpha-amino acid from the hydrolyzate and recovering the remaining D-alpha-amino acid amide.Type: GrantFiled: February 21, 1986Date of Patent: April 17, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masaharu Doya, Toshio Kondo, Hideo Igarashi, Takako Uchiyama
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Patent number: 4898863Abstract: This invention provides a series of novel heterocyclic carboxamides of formula I in which the group --Y--Z< is selected from --C(Ra).dbd.C<, --N.dbd.C<, and --CH(Ra)--CH< and the other radicals have the meanings defined in the following specification.The compounds of formula I are leukotriene antagonists. The invention also provides pharmaceutically acceptable salts of the formula I compounds; pharmaceutical compositions containing the formula I compound, or their salts, for use in the treatment of, for example, allergic or inflammatory diseasxes, or endotoxic or traumatic shock conditions; and processes for the manufacture of the formula I compounds, as well as intermediates for use in such manufacture.Type: GrantFiled: April 15, 1987Date of Patent: February 6, 1990Assignee: ICI Americas Inc.Inventors: Frederick J. Brown, Ying K. Yee
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Patent number: 4894386Abstract: This invention provides a series of novel heterocyclic aliphatic carboxamides of formula I in which the group >Z--Y--X< is selected from >C.dbd.CH--N<, >N--CH.dbd.C<, >C.dbd.N--N< and >N--N.dbd.C< and the other radicals have the meanings defined in the following specification. The compounds of formula I are leukotriene antagonists. The invention also provides pharmaceutically acceptable salts of the formula I compounds; pharmaceutical compositions containing the formula I compound, or their salts, for use in the treatment of, for example, allergic or inflammatory diseases, or endotoxic or traumatic shock conditions; and processes for the manufacture of the formula I compounds, as well as intermediates for use in such manufacture.Type: GrantFiled: October 11, 1988Date of Patent: January 16, 1990Assignee: ICI Americas Inc.Inventors: Frederick J. Brown, Victor G. Matassa
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Patent number: 4855447Abstract: 2-Amino-3-aroyl-.gamma.-oxobenzenebutanoic acids and derivatives having the formula: ##STR1## wherein X is hydrogen, halogen, or loweralkyl; Y is hydrogen, halogen, loweralkyl, loweralkoxyl, nitro, or trifluoromethyl; n is 1 or 2; and R is hydrogen lower-alkyl, or a pharmaceutically acceptable cation, are disclosed having anti-inflammatory activity.Type: GrantFiled: August 8, 1988Date of Patent: August 8, 1989Assignee: A. H. Robins Company, IncorporatedInventor: David A. Walsh
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Patent number: 4849443Abstract: A compound of the formula ##STR1## wherein A is the residue of a ACOOH pyrethrinoid acid, Z is selected from the group consisting of hydrogen, --CN, --C.tbd.CH, --CH.sub.3 and alkyl of 1 to 3 carbon atoms, R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, cycloalkyl, cycloalkenyl and cycloalkynyl of 3 to 8 carbon atoms, aryl of 6 to 14 carbon atoms and aralkyl of 7 to 18 carbon atoms and R.sub.2 is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, cycloalkyl, cycloalkenyl and cycloalkynyl of 3 to 8 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CN, --CF.sub.3, --NO.sub.2 and --COOAlK and AlK is alkyl of 1 to 18 carbon atoms having pesticidal activities.Type: GrantFiled: September 14, 1987Date of Patent: July 18, 1989Assignee: Roussel UclafInventors: Jean Tessier, Jacques Demassey, Jean-Pierre Demoute
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Patent number: 4843081Abstract: A and A' are each hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy or aryloxy;X is cyano, nitro, COOR, SR, SOR or SOOR;R is H, C.sub.1-6 alkyl or aryl;n n' and n" are each 0 to 4; andm, m' and m" are each 1 to 4, have calcium channel blocking activity.Type: GrantFiled: June 27, 1988Date of Patent: June 27, 1989Assignee: Rorer Pharmaceutical CorporationInventors: John R. Regan, Jeffrey N. Barton, John T. Suh, Jerry W. Skiles
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Patent number: 4843091Abstract: An N-sulphonamidoethyl-indole of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, difluoromethoxy, aryl, arylthio, aralkyl, aralkoxy, aralkylthio, acyl or a group of the formula ##STR2## in which R.sup.5 and R.sup.6 are identical or different and denote hydrogen, alkyl, aryl, aralkyl or acyl, andR.sup.3 represents hydrogen, alkyl, aryl, pyridyl, thienyl or furyl, andR.sup.4 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, aryl, aryloxy, arylthio, aralkyl, aralkoxy, aralkylthio, acl or a group of the formula ##STR3## in which R.sup.7 and R.sup.8 are identical or different and denote hydrogen, alkyl, aryl, aralkyl or acyl,R.sup.5 represents hydrogen, ##STR4## or a pharmacologically acceptable salt of ##STR5## and R.sup.2 represents hydrogen, alkyl or aryl.The compounds were R.sup.Type: GrantFiled: June 5, 1987Date of Patent: June 27, 1989Assignee: Bayer AktiengesellschaftInventors: Ulrich Rosentreter, Horst Boshagen, Folker Lieb, Hermann Oediger, Volker-Bernd Fiedler, Elisabeth Perzborn, Friedel Seuter
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Patent number: 4840963Abstract: Novel 2-sulfamoyl-1H-indoles and derivatives thereof are shown to be useful for the treatment of elevated intraocular pressure in pharmaceutical compositions designed for systemic or topical ophthalmic administration.Type: GrantFiled: December 7, 1984Date of Patent: June 20, 1989Assignee: Merck & Co., Inc.Inventors: Kenneth L. Shepard, Samuel L. Graham
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Patent number: 4837235Abstract: This invention provides a series of novel keto sulfones of formula I ##STR1## in which the group .dbd.A-- is selected from .dbd.C(Ra)-- and .dbd.N-- and the other radicals have the meanings defined in the following specification.The compounds of formula I are leukotriene antagonists. The invention also provides pharmaceutically acceptable salts of the formula I compounds; pharmaceutical compositions containing the formula I compound, or their salts, for use in the treatment of, for example, allergic or inflammatory diseases, or endotoxic or traumatic shock conditions; and processes for the manufacture of the formula I compounds, as well as intermediates for use in such manufacture.Type: GrantFiled: October 16, 1986Date of Patent: June 6, 1989Assignee: ICI Americas Inc.Inventors: Peter R. Bernstein, Frederick J. Brown, Victor G. Matassa, Ying K. Yee
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Patent number: 4831156Abstract: The disclosure relates to compounds of the formula ##STR1## and pharmaceutically acceptable addition salts thereof wherein X represents a substituted or unsubstituted alkylene chain containing 1 to 4 carbon atoms, wherein R.sub.5 is a lower alkyl group, wherein R.sub.6 is either hydrogen or methyl, R.sub.9 is hydrogen or lower alkyl, wherein Am is selected from the class consisting of amino, lower mono and dialkylamino, piperidino, piperazino, N-lower alkyl piperazino, pyrrolidino, and morpholino groups, wherein Y.sub.1 and Y.sub.2 are identical and are hydrogen, halogen, methyl or ethyl and n is an integer in the range of 1-5.Type: GrantFiled: September 30, 1987Date of Patent: May 16, 1989Assignee: The University of Tennessee Research Corp.Inventors: Thomas P. Kennedy, George W. Kabalka