Hydroxy Bonded Directly At The 3-position And Oxygen Double Bonded Directly At The 4-position Of The Hetero Ring (h Of -oh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 549/418)
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Patent number: 5602262Abstract: A process for producing intermediate compounds 2-deoxy 2,2-difluoro-.beta.-D-ribo-pentopyranose (III) from 3,3-difluoro-4,5,6-O-trihydroxy-5,6-O-(1-ethylpropylidene)hexene (I). The process of preparing intermediate compound (I) involves reacting D-glyceraldehyde pentanide with an organometallic complex of 3-bromo-3,3-difluoropropene. The process of preparing intermediate compound (III) involves ozonolysis and then hydrolysis. The intermediate compounds (I) and (III) are used in the preparation of 2'-deoxy-2',2'-difluorocytidine which is an antiviral agent.Type: GrantFiled: February 3, 1995Date of Patent: February 11, 1997Assignee: Eli Lilly and CompanyInventor: David D. Wirth
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Patent number: 5536850Abstract: The present invention relates to a novel substance DC114-A1 represented by the following formula (I): ##STR1##Type: GrantFiled: March 1, 1995Date of Patent: July 16, 1996Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Hirofumi Nakano, Noboru Fujii, Tamio Mizukami, Youichi Uosaki, Katsunori Kita, Eiji Kobayashi
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Patent number: 5523421Abstract: Disclosed herein is novel kojic acid derivatives represented by the following formula (I): ##STR1## wherein, R.sub.1 is a hydrogen atom or hydroxyl group; and R.sub.2 is a hydroxyl group, having a strong activity of inhibiting tyrosinase, which is involved in a melanin formation.The compounds of the present invention shows a stronger tyrosinase-inhibiting and radical scavenging activities, and has a low side effects to the human skin.Type: GrantFiled: November 14, 1994Date of Patent: June 4, 1996Assignee: Pacific CorporationInventors: Chang M. Yang, Jong Y. Hong, Ki W. Lee, Byeong G. Lee, Dong I. Chang
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Patent number: 5486624Abstract: Kojic acid derivatives of the following formula (I) ##STR1## where R is a hydrogen atom or methyl group, as radical scavengers and strong inhibitors of tyrosinase, an enzyme involved in a melanin formation.Type: GrantFiled: January 19, 1995Date of Patent: January 23, 1996Assignee: Pacific CorporationInventors: Chang M. Yang, Jong Y. Hong, Ki W. Lee, Byeong G. Lee, Dong I. Chang
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Patent number: 5440053Abstract: Disclosed is a process for recovering maltol from water-insoluble source material containing maltol, comprising extracting the maltol with a hot aqueous solution containing a solute which increases the immiscibility between said source material and said solution.Type: GrantFiled: May 9, 1994Date of Patent: August 8, 1995Assignee: Florasynth, Inc.Inventors: Alexander Fleisher, Yan Gorenshteyn, Ilya Nakhimovich, Olga Vselyubsvaya
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Patent number: 5334518Abstract: Disclosed is a novel process for the production of pyrocomenic acid [3-hydroxy-4(1H)-pyran-4-one and rubiginol [3,5-dihydroxy-4(1H)-pyran-4-one, which are starting materials for synthesis of maltols useful as food spices as well as additives for cosmetics.The chemical reactions possibly taking place in the fermentation and the heating post-treatment thereof in the present invention are shown as follows: ##STR1## The microorganisms usable in the above oxidation fermentation include Gluconobacter rubiginosus IFO 3244, Gluconobacter suboxydans IFO 3254, Gluconobacter melanogenus IFO 3293, Pseudomonas fluorescens IFO 3081, Erwinia carotovara IFO 3380 etc.Type: GrantFiled: November 3, 1992Date of Patent: August 2, 1994Assignee: Yakurigaku Chuo KenkyushoInventors: Hidehiko Takahashi, Katsumi Imada, Akira Motoshio
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Patent number: 5231190Abstract: Squarylium compounds of the formula: ##STR1## wherein Q.sup.1 and Q.sup.2 are each independently a pyrylium, thiopyrylium, selenopyrylium, benzpyrylium, benzthiopyrylium or benzselenopyrylium nucleus, and R.sup.1 and R.sup.2 are each independently an aliphatic or cycloaliphatic group, can be prepared by reacting a squaric acid derivative of the formula: ##STR2## with a compound of the formula Q.sup.2 CH.sub.2 R.sup.2 in the presence of a base. The derivatives of Formula II may be prepared by condensing a 2,3,4,4-tetrahalocyclobut-2-en-1-one with a compound of the formula Q.sup.1 CH.sub.2 R.sup.1 in the presence of a base to produce a compound of the formula: ##STR3## wherein Q.sup.1 and R.sup.1 are as defined above, and X represents chlorine or bromine, and hydrolyzing the compound of Formula III. Alternatively, the derivatives of Formula II may be prepared by reacting a diester, monoacid chloride monoester or diacid chloride of squaric acid with a compound of the formula Q.sup.1 CH.sub.2 R.sup.Type: GrantFiled: May 6, 1991Date of Patent: July 27, 1993Assignee: Polaroid CorporationInventors: Donald A. McGowan, Paulina P. Garcia, John W. Lee, Thomas K. Spencer, Stephen J. Telfer, Michael J. Zuraw
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Patent number: 5221756Abstract: Pure maltol is recovered from maltol containing mixture by co-distillation with an aliphatic or cylcloaliphatic hydrocarbon or hydrocarbon mixture in which the maltol is substantially insoluble.Type: GrantFiled: February 21, 1992Date of Patent: June 22, 1993Assignee: Florasynth, Inc.Inventors: Alexander Fleisher, Richard J. Coleman, Guy J. Gloor, Yan Gorenshteyn
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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: 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: 5077411Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migrains, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.Type: GrantFiled: June 21, 1990Date of Patent: December 31, 1991Assignee: Warner-Lambert Co.Inventors: David T. Connor, Daniel L. Flynn
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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: 4545982Abstract: Novel acyl compounds 3-acyloxy-4(H)-pyran-4-ones were obtained by reacting 3-hydroxy-4(H)-pyran-4-one with acyl halides. The acyl compounds and their starting compound exhibit a skin-lightening effect on the skin and are preferably used as an active constituent in skin-lightening cosmetic preparations or local demelanizing agents.Type: GrantFiled: March 17, 1982Date of Patent: October 8, 1985Assignee: Yakurigaku Chuo KenkyushoInventor: Hidehiko Takahashi
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Patent number: 4443621Abstract: p-Nitrophenyl 3-bromo-2,2-diethoxypropionate, useful in the synthesis of highly functionalized small molecules and heterocycles, including pyromeconic acid and 6-methylpyromeconic acid.Type: GrantFiled: March 14, 1983Date of Patent: April 17, 1984Assignee: Pfizer Inc.Inventors: John L. LaMattina, Paul D. Weeks
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Patent number: 4435584Abstract: 2-Methyl-3-hydroxy-4H-pyran-4-one is prepared by contacting 1(2-furyl)-1-ethanol in aqueous solution with two equivalents of a halogen oxidant at room temperature and then heating until the hydrolysis of the formed 4-halo-dihydropyran intermediate is substantially complete. Other valuable related gamma-pyrones are prepared in analogous manner from appropriate alcohols.Type: GrantFiled: July 19, 1982Date of Patent: March 6, 1984Assignee: Pfizer Inc.Inventors: Thomas M. Brennan, Daniel P. Brannegan, Paul D. Weeks, Donald E. Kuhla
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Patent number: 4390709Abstract: Maltol (3-hydroxy-2-methyl-gamma-pyrone) is prepared from furfural through intermediates (a) 1-(2-furyl)-1-ethanol; (b) 2-(1-hydroxyethyl)-2,5-dialkoxy-2,5-dihydrofuran; (c) alkyl or aralkyl-2-methyl-2H-pyran-3(6H)-one; and (d) 2-alkyl or aralkyl-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-5-one.Pyromeconic acid (3-hydroxy-gamma-pyrone), ethyl maltol (3-hydroxy-2-ethyl-gamma-pyrone) and other valuable 2-substituted-3-hydroxy-gamma-pyrones are prepared in an analogous manner from furfural.Type: GrantFiled: April 26, 1982Date of Patent: June 28, 1983Assignee: Pfizer Inc.Inventors: Paul D. Weeks, Robert P. Allingham
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Patent number: 4368331Abstract: (2-methyl-3-hydroxy-4h-pyran-4-one is prepared by contacting 1(2-furyl)-1-ethanol in aqueous solution with two equivalents of a halogen oxidant at room temperature and then heating until the hydrolysis of the formed 4-halo-dihydro-pyran intermediate is substantially complete. Other valuable related gamma-pyrones are prepared in analogous manner from appropriate alcohols.Type: GrantFiled: November 13, 1979Date of Patent: January 11, 1983Assignee: Pfizer Inc.Inventors: Thomas M. Brennan, Daniel P. Brannegan, Donald E. Kuhla, Paul D. Weeks
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Patent number: 4342875Abstract: Compounds of the formula ##STR1## are prepared and are used as ultraviolet light and weathering stabilizers for polymers, preferably polypropylene. In the formula R is alkoxyphenyl, dialkoxyphenyl or alkylene dioxyphenyl, the alkoxy groups have 1 to 8 carbon atoms and the alkylene group has 1 to 4 carbon atoms, q is 1 to 6, and Z is ##STR2## where R' is H or a 1 to 4 carbon alkyl, R.sup.7 is hydrogen or ##STR3## where R.sup.8 is hydrocarbyl, m is 1 to 4, n is 0 or 1 and m+n is 1 to 4; ##STR4## where R.sup.12 is lower alkyl and G is H or ##STR5## and where at least one of the n's is zero. ##STR6## where s is 1 to 3 and t is from 0 to 2, the total of s and t being not over 3; ##STR7## where u is 2 to 4; ##STR8## where v and w are each 1 to 4 and p is 2 to 4; ##STR9## where R" and R"' are 1 to 8 carbon atom alkyl or where R.sup.11 and R.sup.111 together with the oxygen atoms attached thereto and the adjacent carbon atoms of the benzene ring form a 5 or 6 membered heterocyclic ring and R.sup.Type: GrantFiled: January 9, 1974Date of Patent: August 3, 1982Assignee: Cincinnati-Milacron, Inc.Inventor: Robert G. Gough
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Patent number: 4342697Abstract: Maltol (3-hydroxy-2-methyl-gamma-pyrone) is prepared from furfural through intermediates (a) 1-(2-furyl)-1-ethanol; (b) 2-(1-hydroxyethyl)-2,5-dialkoxy-2,5-dihydrofuran; (c) alkyl or aralkyl-2-methyl-2H-pyran-3(6H)-one; and (d) 2-alkyl or aralkyl-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-5-one.Pyromeconic acid (3-hydroxy-gamma-pyrone), ethyl maltol (3-hydroxy-2-ethyl-gamma-pyrone) and other valuable 2-substituted-3-hydroxy-gamma-pyrones are prepared in an analogous manner from furfural.Type: GrantFiled: November 11, 1976Date of Patent: August 3, 1982Assignee: Pfizer Inc.Inventors: Paul D. Weeks, Robert P. Allingham