Plural Chalcogens Bonded Directly To The Hetero Ring Patents (Class 549/417)
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Patent number: 5354873Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an aromatic unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an acyl, aliphatic, cycloaliphatic, aromatic or heterocyclic group, subject to the proviso that one of R.sup.3 and R.sup.4 may be an amino or substituted amino group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a nitrogenous heterocyclic ring) are useful as near infra-red absorbers.Type: GrantFiled: November 20, 1992Date of Patent: October 11, 1994Assignee: Polaroid CorporationInventors: Richard M. Allen, Peter K. Chu, John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
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Patent number: 5349070Abstract: The present invention relates to a novel salicylic acid-maltol conjugates of the formula I. ##STR1## wherein R represents H, alkyl groups containing C.sub.1-5 carbon atoms or alkanoyl groups containing C.sub.1-5 carbon atoms. R.sub.1 represents H or alkyl groups containing C.sub.1-5 carbon atoms.A novel maltol esters of salicylic acid derivatives exhibit antioxidant and antithrombotic activities to a greater extent than salicylic acid derivatives.Type: GrantFiled: February 19, 1993Date of Patent: September 20, 1994Inventor: Byung H. Han
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Patent number: 5334614Abstract: The invention concerns hydroxylamine derivatives of the formula I ##STR1## wherein R.sup.4 is hydrogen, carbamoyl, (1-4C)alkyl, cyclopentyl, cyclohexyl, tetrahydrofuran-3-yl, tetrahydropyran-4-yl, piperidin-4-yl, N-(1-4C)alkylpiperidin-4-yl, (2-5C)alkanoyl, (1-4C)alkylsulphonyl, N-(1-4C)alkylcarbamoyl, N,N-di-(1-4C)alkylcarbamoyl, phenyl, phenyl-(1-4C)alkyl, di-phenyl-(1-4C)alkyl, benzoyl, phenylsulphonyl or a heteroarylmethyl group;R.sup.5 is hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl;A.sup.4 is (1-4C)alkylene;Ar.sup.1 is phenylene, pyridinediyl or pyrimidinediyl;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, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl or thiazolediyl;R.sup.1 is hydrogen, (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 -wherein each of A.sup.2 and A.sup.Type: GrantFiled: May 11, 1993Date of Patent: August 2, 1994Assignees: Zeneca Ltd., Zeneca Pharma SAInventors: Philip N. Edwards, Michael S. Large
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Patent number: 5334616Abstract: The compounds of the present invention comprise substituted phenolic thioethers represented by the formula(I) and the radicals are defined in the claims: ##STR1## The compounds of the present invention are useful in the treatment of local and systemic inflammation and allergy reactions.Type: GrantFiled: June 22, 1993Date of Patent: August 2, 1994Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 5332757Abstract: 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: February 8, 1993Date of Patent: July 26, 1994Assignees: Zeneca Limited, Zeneca PHARMA S AInventors: Thomas G. C. Bird, Patrick Ple
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Patent number: 5314891Abstract: The invention concerns benzenesulphonamide derivatives of the formula I ##STR1## wherein R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl;R.sup.2 and R.sup.3 together form --A.sup.2 --X.sup.2 --A.sup.3 -- which defines a ring having 5 or 6 ring atoms, wherein A.sup.2 and A.sup.3 each is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio or imino;Ar is optionally substituted phenylene;R.sup.4 is (1-4C)alkyl, fluoro-(2-4C)alkyl or optionally substituted phenyl or a heterocyclic moiety;R.sup.5 is hydrogen or (1-4C)alkyl; andR.sup.6 is hydrogen, halogeno, trifluoromethyl, (1-4C)alkyl or (1-4C)alkoxy;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.Type: GrantFiled: September 10, 1992Date of Patent: May 24, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Philip N. Edwards, Keith Oldham, David Waterson
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Patent number: 5304660Abstract: The invention provides compounds of formula (I) wherein R.sup.1 represents alkyl, R.sup.2 represents an acid-labile protecting group and X.sup.1 represents a halogen atom, which are useful in the synthesis of mevalonic acid derivatives.Type: GrantFiled: August 11, 1992Date of Patent: April 19, 1994Assignee: Rhone-Poulenc Rorer S.A.Inventors: Stanley F. Clark, Ronald H. Jones, Christopher G. Newton
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Patent number: 5296616Abstract: There is disclosed an optically active fluorine-containing compound represented by the general formula (I) ##STR1## wherein Rf is a fluoroalkyl group having 1 or 2 carbon atoms; R.sup.1, R.sup.2 and R.sup.3, independently of one another, are each a hydrogen atom, a straight or branched chain alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms or an aralkyl group having 7 to 10 carbon atoms; and * is an asymmetric carbon atom. The above compound has a fluoroalkyl group with a remarkable electron-attracting property at the asymmetric carbon atom in the tetrahydropyran ring. It is exemplified by tetrahydro-6-trifluoromethyl-2-hexyloxy-4-methyl-5-hydroxypyran and expected to find a wide variety of useful applications as raw materials for an enzyme inhibitor, a bioactive substance, a carcinostatic, a ferroelectric liquid crystal, etc.Type: GrantFiled: December 11, 1992Date of Patent: March 22, 1994Assignee: Kashima Oil CompanyInventors: Masaaki Namekawa, Shinichi Nayuki, Keizou Itoh, Mitsunori Takeda, Yoshinobu Murayama
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Patent number: 5294723Abstract: A salt of glucopyranose derivative of the formula (I) ##STR1## wherein R.sup.2 is ##STR2## R.sup.3 is ##STR3## Y.sup.+ is sodium ion or tris(hydroxymethyl)methylammonium ion; and a glucopyranose derivative of the formula (II) ##STR4## wherein all the symbols are the same meaning as hereinbefore defined, is an important intermediate for the preparation of compound of the formula (I).Type: GrantFiled: January 28, 1993Date of Patent: March 15, 1994Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Katsuhiro Imaki, Shinsuke Hashimoto, Hirohisa Wakatsuka
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Patent number: 5294725Abstract: A novel antibiotic substance, Scopularin, is prepared by cultivation of a strain of the microorganism, Scopulariopsis, A.T.C.C. No. 20,914. This compound and its alcohol derivative have also been found to have cytochrome P450 inhibition activity.Type: GrantFiled: January 31, 1989Date of Patent: March 15, 1994Assignee: E. R. Squibb & Sons, Inc.Inventors: Donald R. Kirsch, Joseph O'Sullivan, Douglas W. Phillipson
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Patent number: 5292885Abstract: 2,3,5-(4H)-Trimethyl pyranone having the formula: ##STR1## which is prepared by acetylation of a ketone derived from 2-formyl-3-pentanone and preparation of 2,3,5-(1H)-trimethyl 4-pyridinone having the formula: ##STR2## by ammonolysis of the 2,3,5-(4H)-trimethyl 4-pyranone.Type: GrantFiled: August 13, 1990Date of Patent: March 8, 1994Assignee: IsochemInventors: Didier G. Wirth, Dominique Gibert, Laurence Ferrucio
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Patent number: 5281720Abstract: 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: October 26, 1992Date of Patent: January 25, 1994Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Yves Girard, John W. Gillard, Laird A. Trimble, John Scheigetz, James A. Yergey, Yves Ducharme, Deborah A. Nicoll-Griffith, John H. Hutchinson
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Patent number: 5270334Abstract: Novel antibiotic substances, including novel natural products, having the general formula ##STR1## wherein R.sub.1 and R.sub.2 are as defined herein, are disclosed. These compounds have been found to be cytochrome P450 inhibitors.Type: GrantFiled: July 1, 1992Date of Patent: December 14, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: Joseph O'Sullivan, Douglas W. Phillipson, Henner Straub, Peter H. Ermann
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Patent number: 5262552Abstract: An optically active (S)- or (R)-pentane compound of the general formula (11): ##STR1## wherein R.sub.11, R.sub.12 and R.sub.13 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R.sub.14 represents a hydroxy, protected hydroxy or oxo group, if R.sub.14 is an oxo group, the ring denoting benzene in the above formula (11) is benzoquinone, R.sub.15 represents a hydrogen atom, hydroxy or acyloxy group, R.sub.16 represents a hydroxy or acyloxy group, and the chiral central carbon marked with a symbol * in said formula (11) alternatively has one of an R-configuration and an S-configuration, is disclosed. Further, intermediate products of the compound of the formula (11) are also disclosed. Still further, a process for manufacturing the above compounds is disclosed. The compound of the formula (11) is easily synthesized from an easily available optically active starting material.Type: GrantFiled: February 20, 1991Date of Patent: November 16, 1993Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5254581Abstract: The invention concerns a cyclic ether derivative of the formula I ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a 9- or 10-membered bicyclic heterocyclic moiety;A.sup.1 is a direct link to X.sup.1 or (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar.sup.2 is optionally substituted phenylene or pyridylene;R.sup.1 includes hydrogen, (1-4C)alkyl, (1-4C)alkcxycarbonyl and (1-4C)alkylthio; 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, defines a ring having 5 to 7 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: February 2, 1993Date of Patent: October 19, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Pierre A. R. Bruneau, Robert I. Dowell, David Waterson
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Patent number: 5250567Abstract: The compounds of the present invention comprise substituted phenolic thioethers represented by the formula (I): ##STR1## wherein: R.sup.1 and R.sup.2 are the same or different and independently represent tert-alkyl or phenyl; R.sup.3 represents hydrogen or alkyl; X represents --(CH.sub.2).sub.w --B--(CH.sub.2).sub.y -- wherein B represents O, S, or CH.sub.2 and w and y can each independently be an integer from 0 to 3 with the proviso that the sum of w+y is equal to or less than 3; A represents O or S(O).sub.n wherein n is 0, 1 or 2; p is an integer from 1 to 4; and R represents alkyl; OH; OR.sup.4 wherein R.sup.4 is alkyl of 1 to 4 carbon atoms; NR.sup.5 R.sup.6 wherein R.sup.5 is hydrogen or alkyl and R.sup.6 is hydrogen, alkyl, heterocyclealkyl in which the hetercyclic ring may optionally be substituted; cycloalkyl; substituted cycloalkyl; phenyl; substituted phenyl; phenylalkyl; or substituted phenylalkyl; or NR.sup.5 R.sup.Type: GrantFiled: June 24, 1992Date of Patent: October 5, 1993Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 5250505Abstract: Cyclohexenone oxime ethers I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, A is unsubstituted or substituted C.sub.3 -C.sub.6 -alkynylene, Z is unsubstituted or substituted phenyl an unsubstituted or substituted 6-membered or 7-membered saturated or monounsaturated or diunsaturated heterocyclic structure having one or two hetero atoms selected from the group consisting of oxygen and sulfer, and their agriculturally useful salts and esters of C.sub.1 -C.sub.10 -carboxylic acids and inorganic acids, are suitable as herbicides.Type: GrantFiled: May 8, 1991Date of Patent: October 5, 1993Assignee: BASF AktiengesellschaftInventors: Juergen Kast, Norbert Meyer, Ulf Misslitz, Albrecht Harreus, Thomas Kuekenhoehner, Harald Bang, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter
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Patent number: 5239091Abstract: The present invention relates to 2-deoxy-N-acetyl-neuraminic acid derivatives and methods for their preparation.Type: GrantFiled: November 7, 1991Date of Patent: August 24, 1993Assignee: G. D. Searle & Co.Inventors: Chi-Huey Wong, William J. Hennen
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Patent number: 5236948Abstract: The invention concerns sulphonamide derivatives of the formula I ##STR1## wherein R.sup.1 includes (1-4C)alkyl;R.sup.2 and R.sup.3 together form --A.sup.2 --X.sup.2 --A.sup.3 -- which defines a ring having 5 to 7 ring atoms, wherein A.sup.2 and A.sup.3 each is (1-3 C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;A.sup.1 is a direct link to X.sup.1 or is (1-3 C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is optionally substituted phenylene or Ar is pyridylene;Q is nitrogen or of the formula CR.sup.7, wherein R.sup.7 includes hydrogen, halogeno, (1-4 C)alkyl and (1-4 C)alkoxy;each of R.sup.4 and R.sup.5 is (1-4 C)alkyl, (3-4 C)alkenyl, (3-4 C)alkynyl or optionally substituted phenyl, benzyl or pyridyl, or R.sup.5 may be hydrogen; andR.sup.6 has any of the meanings defined for R.sup.7 ;or a pharmaceutically-acceptable salt thereof; processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.Type: GrantFiled: January 10, 1992Date of Patent: August 17, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventor: David Waterson
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Patent number: 5236694Abstract: .sup.19 F labelled compounds are disclosed which are useful in methods of NMR imaging and spectroscopy. The compounds comprise a .sup.19 F-containing sensor moiety, and a transport polymer or substrate, and can optionally also comprise a spacer moiety to separate the sensor moiety and the transport polymer.Type: GrantFiled: February 21, 1990Date of Patent: August 17, 1993Assignee: The Board of Regents, The University of Texas SystemInventors: Peter P. Antich, Padmakar V. Kulkarni
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Patent number: 5233056Abstract: An optically active (S)- or (R)-chroman-2-ethanol compound of a general formula (I) ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and a chiral central carbon atom marked with a symbol * in the formula (I) alternatively has one of an R-configuration and an S-configuration, is disclosed. Further, intermediate products of the compound of the formula (I) are also disclosed. Still further, a process for manufacturing the above compounds is disclosed. The compound of the formula (I) is easily synthesized from an easily available optically active starting material.Type: GrantFiled: November 8, 1991Date of Patent: August 3, 1993Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5225438Abstract: The invention concerns an aryl derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X.sup.1 is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X.sup.1 is a group of the formula--X.sup.4 --CR.sub.2 -- or --CR.sub.2 --X.sup.4 --whereinX.sup.4 is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl;each of Ar.sup.2 and Ar.sup.3 is optionally substituted phenylene;X.sup.2 is oxy, thio, sulphinyl or sulphonyl;R.sup.1 is (1-4C)alkyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X.sup.3 --A.sup.2 -- which together with the carbon atom to which A.sup.1 and A.sup.2 are attached define a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X.sup.Type: GrantFiled: November 26, 1991Date of Patent: July 6, 1993Assignees: Imperial Chemical Industries PLC, I.C.I.-PharmaInventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
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Patent number: 5217991Abstract: Non-peptidyl compounds characterized generally as cycloalkyl/cycloalkylalkyl-N-terminal cycloalkoxy-C-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from cycloalkyl and cycloalkylalkyl groups, wherein said cycloalkyl group contains three to about eight carbon atoms and the acyclic alkyl portion of said cycloalkylalkyl group contains one to about eight carbon atoms; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl: wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 and R.sub.Type: GrantFiled: May 28, 1992Date of Patent: June 8, 1993Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
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Patent number: 5216013Abstract: Non-peptidyl compounds characterized generally as heterocyclic acyl aminodiol .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are compounds of the formula ##STR1## wherein R.sub.1 is selected from aryl and aralkyl groups represented by ##STR2## and wherein R.sub.1 may be further selected from heteroaryl and heteroaralkyl represented by ##STR3## wherein each of T and A is independently selected from N and CH; wherein n is a number selected from zero through five, inclusive; wherein X is selected from oxygen atom, methylamino and NH; wherein each of Y and Z is independently selected from chloro, fluoro, methoxy and dimethylamino; wherein Q is oxygen atom; and wherein each of T and A is independently selected from N and CH; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is selected from methyl and ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; wherein R.Type: GrantFiled: July 16, 1992Date of Patent: June 1, 1993Assignee: G. D. Searle & Co.Inventor: Gunnar J. Hanson
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Patent number: 5210238Abstract: Perfluorinated cyclic hemiketals of formula: ##STR1## where n=1-6, m=2-3, and their corresponding perfluoridiketones. The latter are prepared by means of perfluoroalkylation reaction of diacyl fluorides with perfluoroalkyl-trialkyl silanes. The perfluorodiketones can be then reacted with H.sub.2 O in order to obtain said cyclic hemiketals.Type: GrantFiled: January 23, 1992Date of Patent: May 11, 1993Assignee: Ausimont S.p.A.Inventors: John D. Anderson, Darryl D. Desmarteau, Walter Navarrini
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Patent number: 5208259Abstract: The invention concerns a diaryl ether heterocycle of the formula I, or a pharmaceutically-acceptable salt thereof, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is optionally substituted phenylene, or a 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is (1-4C)alkylene and X.sup.2 is oxy, thio, sulphinyl, sulphonyl or imino.The invention also concerns processes for the manufacture of a diaryl ether heterocycle of the formula I, or a pharmaceutically-acceptable salt thereof, and pharmaceutical compositions containing said heterocycle. The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: July 3, 1990Date of Patent: May 4, 1993Assignees: Imperial Chemical Industries, ICI PharmaInventors: Thomas G. C. Bird, Philip N. Edwards
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Patent number: 5190573Abstract: Cyclohexenone oxime ethers ##STR1## where R.sup.1 is alkyl;A is substituted or unsubstituted alkylene or alkenylene, where methylene is replaced by an oxygen atom, a sulfur atom, a sulfoxyl group, a sulfonyl group or --NR.sup.a --,Z is phenyl or a 5- or 6-membered heteroaromatic structure;X is substituted or unsubstituted amino, nitro, cyano, halogen, 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 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbony or phenyl;n is 0 to 3, or 1 to 5 where X is halogen;R.sup.Type: GrantFiled: May 8, 1991Date of Patent: March 2, 1993Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Norbert Goetz, Albrecht Harreus, Bruno Wuerzer, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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Patent number: 5155240Abstract: A process for producing an optically active dihydropyran derivative represented by formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each represents a hydrogen atom, a lower alkyl group, a tri-lower alkylsilylmethyl group, a lower alkoxycarbonylamino group, or an --OR.sup.5 group, wherein R.sup.5 represents a lower alkyl group, a lower acyl group, a lower alkoxycarbonyl group, a di-lower alkylcarbamoyl group, or a tri-lower alkylsilyl group, or R.sup.1 and R.sup.2 are taken together to form a 5- to 7-membered cyclic hydrocarbon group or to form a condensed heterocyclic group with an oxygen atom, or R.sup.2 and R.sup.3 are taken together to form a 5- to 7-membered cyclic hydrocarbon group or to form a condensed heterocyclic group with an oxygen atom, provided that all of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 do not represent hydrogen atoms at the same time; and R.sup.6 represents a lower alkyl group, which comprises reacting a diene compound represented by formula (2): ##STR2## wherein R.Type: GrantFiled: March 13, 1991Date of Patent: October 13, 1992Assignee: Takasago International CorporationInventors: Koichi Mikami, Masahiro Terada, Takeshi Nakai, Noboru Sayo
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Patent number: 5141954Abstract: A new carbazate represented by the formula ##STR1## is found to be antifungal and especially useful in the treatment of mycotic infections caused by the Cryptococcus species.Type: GrantFiled: July 30, 1991Date of Patent: August 25, 1992Assignee: Merck & Co., Inc.Inventors: Arthur A. Patchett, Frank VanMiddlesworth
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Patent number: 5126500Abstract: A process for preparing retinyl glycosides of the formula I ##STR1## where Z is a glycosidic residue, by glycosidation of a completely acylated carbohydrate or completely acylated glycosidic polymer of the formula IIZ (acylated)-Y (II)where Y is a leaving group customary for glycosidations in the 1-position of the glycoside, comprises the acylated glycoside being reacted with an aldehyde-protected 4-hydroxy-2-methyl-2-buten-1-al under the conditions customary for glycosidations, eliminating the aldehyde protective group from the resulting compound, subjecting the resulting aldehyde to a Wittig reaction with a .beta.-ionylideneethyltriphenylphosphonium salt and eliminating the acyl groups on the resulting retinyl glycoside in a conventional manner.The process according to the invention is particularly important for preparing retinyl glycosides of the formula Ia ##STR2## where R is --CH.sub.2 --OH, --COOH or --COOCH.sub.3. Intermediates of this process are also claimed.Type: GrantFiled: January 28, 1991Date of Patent: June 30, 1992Assignee: BASF AktiengesellschaftInventors: Ulrich von Deessen, Joachim Paust, Klaus Kaiser, Helmut Indest
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Patent number: 5098930Abstract: The invention concerns a heterocyclic derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;A.sup.1 is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo-(3-6C)alkylene;Ar.sup.2 is optionally substituted phenylene, or a 6 membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; andR.sup.2 and R.sup.3 together form a group of the formula -A.sup.2 -X-A.sup.3 - wherein each of A.sup.2 and A.sup.3 is (1-4C)alkylene and X is oxy, thio, sulphinyl, sulphonyl or imino;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: December 22, 1989Date of Patent: March 24, 1992Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Philip N. Edwards, Jean-Marc M. M. Girodeau
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Patent number: 5093505Abstract: Heterocyclic compounds of the general formula: ##STR1## wherein R.sup.11 is a hydroxyl group or a lower alkoxy group, R.sup.12 is a lower alkoxy group, R.sup.13 is a saturated or unsaturated hydrocarbon group, X is an oxygen atom or a sulfur atom, and Y is an oxygen atom or --NH-- which may have a lower alkyl substituent, or salts thereof are novel and effective in controlling carcinoma.Type: GrantFiled: May 25, 1990Date of Patent: March 3, 1992Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Hoyoku Nishino, Yukihiro Kodera, Toshihiko Sumida, Susumu Yoshida, Hiromichi Matsuura, Yoichi Itakura
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Patent number: 5075461Abstract: A process for the manufacture of 3-hydroxy-2-alkyl-4-pyrones of formula I is provided. ##STR1## The process comprises cyclizing a compound of formula II, ##STR2## in acidic medium and hydrolyzing the ester formed thereby to produce compound I. R.sup.1 represents methyl or ethyl; R.sup.2 represents lower alkanoyl or optionally substituted benzoyl; R.sup.3 represents --OH or --NR.sup.4 R.sup.5 ; and, R.sup.4 and R.sup.5 may be alike or different and represent lower alkyl. The pyrones of formula I wherein R.sup.1 represents methyl or ethyl are known flavorants and odorants.Type: GrantFiled: April 19, 1989Date of Patent: December 24, 1991Assignee: Givaudan CorporationInventor: Hans-Jakob Wild
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Patent number: 5049673Abstract: The present invention discloses a new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths. The new fluorescent indicator dyes combine at least one tricyclic chromophore with a tetracarboxylate parent CA.sup.2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium.sup.2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium.sup.2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA.sup.2+ ] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.Type: GrantFiled: October 30, 1987Date of Patent: September 17, 1991Assignee: The Regents of the University of CaliforniaInventors: Roger Y. Tsien, Akwasi Minta
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Patent number: 5022914Abstract: Cyclohexenone oxime ethers of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl,A is substituted or unsubstituted C.sub.4 -alkylene or C.sub.4 -alkenylene,X is nitro, cyano, halogen, 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 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl and/or phenyl,n is from 0 to 3 or from 1 to 5 when X is halogen,R.sup.2 is C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.Type: GrantFiled: October 31, 1989Date of Patent: June 11, 1991Assignee: BASF AktiengesellschaftInventors: Juergen Kast, Dieter Kolassa, Norbert Meyer, Ulrich Schirmer, Albrecht Harreus, Jochen Wild, Karl-Otto Westphalen, Bruno Wuerzer
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Patent number: 5017693Abstract: The present invention provides cleavable conjugates whose linkers contain a labile bond that is cleavable under a variety of mild conditions, including weakly acidic. Since the agent may be bonded directly to the linker, cleavage can result in release of native agent. The invention also provides methods for producing cleavable conjugates. Preferred agents include drugs, toxins, biological response modifiers, radiodiagnostic compounds, radiotherapeutic compounds, and derivatives thereof. The targeting molecule employed in the invention may be an intact molecule, a fragment thereof, or a functional equivalent thereof. In a particularly preferred embodiment, the targeting molecule is a monoclonal antibody directed towards a tumor-associated antigen in man. The invention further provides methods for delivering to the cytoplasm of target cell an agent free of its targeting molecular carrier.Type: GrantFiled: December 19, 1989Date of Patent: May 21, 1991Assignee: NeoRx CorporationInventors: Mark D. Hylarides, Ananthachari Srinivasan, Jeffrey N. Fitzner, Vivekananda M. Vrudhula
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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: 5006150Abstract: Substituted benzoyl-2H-pyran-3,5-(4H,6H)-diones and related compounds, intermediates therefor, synthesis thereof, and the use of said diones for the control of weeds.Type: GrantFiled: May 29, 1990Date of Patent: April 9, 1991Assignee: Sandoz Ltd.Inventors: Shy-Fuh Lee, Richard J. Anderson, Gary W. Luehr, Carole R. Scott
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Patent number: 4952604Abstract: Pyranyl ester compounds isolated from the fermentation of the species Penicillium are described. The compounds are useful as antifungal agents.Type: GrantFiled: May 3, 1989Date of Patent: August 28, 1990Assignee: Merck & Co., Inc.Inventors: Otto D. Hensens, Jerrold M. Liesch, James A. Milligan, Sagrario M. Del Val, Robert E. Schwartz, Carol Wichmann
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Patent number: 4950775Abstract: A method of preparing compactin and mevinolin, ketoacid, enone, and glutarate analogs thereof, and related compounds. The compounds are prepared in substantially enantiomerically pure form using a structurally convergent synthesis. Total syntheses of (+)-compactin, (+)-mevinolin and related compounds are provided. Novel compounds are identified, several of which show significant anti-hypercholesterolemic activity.Type: GrantFiled: October 11, 1985Date of Patent: August 21, 1990Assignee: University of CaliforniaInventors: Clayton H. Heathcock, Terry J. Rosen
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Patent number: 4920231Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible streoisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stereo-specific compound and all possible stereo-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.Type: GrantFiled: March 30, 1989Date of Patent: April 24, 1990Assignee: Roussel UclafInventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
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Patent number: 4914127Abstract: 3-Demethylmevalonic acid derivatives of the formula I (.delta.-lactone) and Ia (corresponding dihydroxycarboxylic acid derivative) ##STR1## in which A-B, Z, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the indicated meanings, a process for the preparation of these compounds, their use as medicaments and pharmaceutical products are described. In addition, new intermediates for the preparation of the compounds of the formula I and Ia are described.Type: GrantFiled: March 8, 1989Date of Patent: April 3, 1990Assignee: Hoechst AktiengesellschaftInventors: Gerhard Beck, Bela Kerekjarto, Hans-Hermann Lau, Gunther Wess
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Patent number: 4908381Abstract: The present invention provides a liquid composition that yields an abrasion resistant polymeric film on a surface that provides extended protection from microbial growth through slow release of a potent antimicrobial agent. The active ingredient of the liquid composition has the following general formula: ##STR1## wherein R=H, (C.sub.1 -C.sub.3)alkyl, --COOH, --CH.sub.2 --COOH, --C.sub.6 H.sub.11, or -phenyl;R'=H, (C.sub.1 -C.sub.3)alkyl, --CH.sub.2 --COOH, --C.sub.6 H.sub.11, or -phenyl;R"=H, or (C.sub.1 -C.sub.5)alkyl; andX=a single bond; ##STR2## where m=2-4; andZ=H or (C.sub.1 -C.sub.3)alkyl; as well as homopolymers, copolymers, or terpolymers comprising said active ingredient.Type: GrantFiled: December 5, 1988Date of Patent: March 13, 1990Assignee: Ecolab Inc.Inventors: Richard B. Greenwald, Isaac S. Y. Sze
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Patent number: 4871761Abstract: Novel pesticides of the formula ##STR1## in which R.sup.1 represents in each case optionally substituted cycloalkyl, cycloalkenyl, tetrahydronaphthyl, decahydronaphthyl, phenyl, naphthyl or thienyl,R.sup.2 represents alkyl,R.sup.3 represents hydrogen alkyl, alkenyl, alkinyl, hydroxyalkyl, alkoxyalkyl, dialkoxyalkyl, hydroxyalkoxyalkyl, cyano or formyl, or in each case optionally substituted cycloaklyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, aralkyl, aryl, furanylmethyl or tetrahydrofuranylmethyl,R.sup.4 represents hydrogen or alkyl, andHet represents an optionally substituted heterocyclic ring of the formula ##STR2## and acid-addition salts thereof.Type: GrantFiled: March 18, 1988Date of Patent: October 3, 1989Assignee: Bayer AktiengesellschaftInventors: Detlef Wollweber, Stefan Dutzmann
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Patent number: 4861788Abstract: Compounds of formula (I): ##STR1## wherein ##STR2## is a 5-membered heterocyclic group having a 6-.pi.electron system, the five ring atoms being either(a) one carbon atom and four atoms selected from carbon and nitrogen,(b) two carbon atoms, two nitrogen atoms and one atom selected from oxygen and sulphur, or(c) four carbon atoms and one atom selected from oxygen and sulphurand R.sup.1 is a substituent on a carbon or nitrogen of ##STR3## selected from C.sub.1-20 alkyl, C.sub.2-8 alkenyl aryl, aralkyl and heterocyclyl, each of which may optionally be substituted; hydrogen and C.sub.3-7 cycloalkyl,and, where appropriate, R.sup.2 is a substituent on a carbon or nitrogen of ##STR4## and when present is the same or different to R.sup.1 and is selected from C.sub.1-20 alkyl, C.sub.2-8 alkenyl, aryl, aralkyl and heterocyclyl each of which may optionally be substituted; hydrogen and C.sub.3-7 cycloalkyl, have antibacterial and antimycoplasmal activity.Type: GrantFiled: January 30, 1987Date of Patent: August 29, 1989Assignee: Beecham Group plcInventors: Norman H. Rogers, Graham Walker, Michael J. Crimmin, Peter J. O'Hanlon
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Patent number: 4855463Abstract: Water soluble glucuronic acid derivatives of vitamin A, including retinoyl .beta.-glucuronide and retinyl .beta.-glucuronide, having in vivo activity comparable to retinoic acid and retinol and methods of their preparation are disclosed.Type: GrantFiled: December 15, 1986Date of Patent: August 8, 1989Assignee: Iowa State University Research Foundation, Inc.Inventors: Arun B. Barua, James A. Olson
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Patent number: 4840957Abstract: A pyran derivative represented by a general formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, cycloalkyl or phenyl, R.sub.2 is alkyl having 8 to 20 carbon atoms, R.sub.3 is hydrogen, halogen, ##STR2## or --CH.sub.2 N A, R.sub.4 and R.sub.5 being each lower alkyl or cycloalkyl, A being --CH.sub.2 13 , oxygen or nitrogen atom, N A forms five or six-member ring (the ring may have no substitutent or have at least one substituent selected from lower alkyl, lower alkoxy and halogen atom), or an acid salt thereof, are useful as agricultural miticides.Type: GrantFiled: January 21, 1988Date of Patent: June 20, 1989Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Hisashi Takao, Norio Osaki, Norio Yasudomi
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Patent number: 4818431Abstract: New tetrahydropyran derivatives of the formula I ##STR1## in which G is H.sub.2 or .dbd.O, R.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, it also being possible for one or two CH.sub.2 groups to be replaced by O atoms, or are F, Cl, Br or CN, R.sup.2 is also H, A.sup.1 and A.sup.2 are each 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl groups which are unsubstituted or substituted by 1-4 F atoms, Z.sup.1 and Z.sup.2 are each --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, or a single bond, m and n are each 0, 1, 2 or 3, but (m+n) is at least 1 and at most 3, it being possible, when m is 2 or 3, for the group A.sup.1 and, when n is 2 or 3, for the groups A.sup.2 each to be identical or different from one another, and the acid addition salts of those among these compounds which are basic, are suitable for use as components in liquid-crystal dielectrics.Type: GrantFiled: November 24, 1986Date of Patent: April 4, 1989Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Joachim Krause, Peter Fuss
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Patent number: 4816062Abstract: The disclosure herein pertains to herbicidal methods and compositions containing 3,5-dicarboxylic acid esters of 2,6-bis-(fluoroalkyl) tetrahydropyrans and piperidines which may be substituted in the 4-position by certain alkyl, phenyalkyl, phenyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, and heterocyclic radicals wherein the hetero atom is oxygen and sulfur and to a process for the preparation thereof. These compounds are useful as pre-emergent herbicides.Type: GrantFiled: June 2, 1986Date of Patent: March 28, 1989Assignee: Monsanto CompanyInventor: Len F. Lee
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Patent number: 4814166Abstract: Anionic oligomers of the general formula: ##STR1## in which T denotes the radical ##STR2## optionally in a mixture with the OH radical; u=0 or 1; p=1 or 2; M=H, Na, K, ammonium or a mono-, di- or tri-(alkyl or hydroxyalkyl)ammonium group, the alkyl part containing 1 to 4 carbon atoms; n=5-30; z=1-6; and R denotes an aliphatic, alicyclic, aryl, alkylaryl or aralkyl radical of valency z, which can contain 1 or more oxygen atoms, it being possible for the formula (I) to contain minor proportions of intermolecular or intra-molecular branches originating from a bis-epoxide.These oligomers are prepared by the addition of n mols of epihalogenohydrin, and optionally of a minor proportions of bis-epoxide, to 1 mol of compoundsR(OH).sub.z (II),in the presence of a Lewis acid, the polyhalogen compounds obtained then being converted into polythiocarboxylic compounds by reaction with a salt or an ester of thiloactic acid, thioglycolic acid or .alpha.-mercaptopropionic or .beta.Type: GrantFiled: May 20, 1986Date of Patent: March 21, 1989Assignee: L'OrealInventors: Guy Vanlerberghe, Henri Sebag