Polycyclo Ring System Patents (Class 568/326)
  • Patent number: 5070207
    Abstract: There is disclosed a method for the treatment of immunoinflammatory conditions, such as allergy, anaphylaxis, asthma, psoriasis, inflammatory bowel disease and inflammation in mammals which comprises administering to a mammal so afflicted an effective amount of a compound having the formula: ##STR1## wherein Z is a group having the formula ##STR2## R.sup.1 and R.sup.2 are each, independently, hydrogen or lower alkyl; R.sup.3 and R.sup.4 are each, independently, hydrogen, alkyl of 1-20 carbon atoms, halo, halo lower alkyl, halo lower alkoxy, lower alkoxy, halo lower alkylsulfonyl, nitro or trifluoromethyl, where at least one of R.sup.3 and R.sup.4 is other than hydrogen;R.sup.5 is hydrogen, lower alkyl or halo;A is --CH.sub.2 --, --O-- or --S--;m is 0-10;n is 1-8;X is hydrogen, fluoro, lower alkyl or aralkyl of 7-12 carbon atoms;or a pharmacologically acceptable salt thereof.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: December 3, 1991
    Assignee: American Home Products Corporation
    Inventors: Guy A. Schiehser, Gregory F. Von Burg
  • Patent number: 5008425
    Abstract: A process which comprises reacting under substantially anhydrous conditions a perfluoroalkyltrihydrocarbylsilane and a carbonyl compound in the presence of a catalyst such that the carbonyl compound is perfluoroalkylated.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: April 16, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4992563
    Abstract: This invention relates to several intermediates useful in preparing thromboxane A.sub.2 inhibiting (.+-.)7-[3.alpha.-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-1.alpha ., 4.alpha.-bicyclo[2.2.1]hept-2.beta.-yl]-heptenoic acids and useful derivatives thereof from (.+-.)octahydro-1.alpha.-methyl-3a.alpha., 7a.alpha.-4.alpha.,7.alpha.-methano-2H-inden-2-ones.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: February 12, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 4945108
    Abstract: New angucyclinones with a therapeutic action can be prepared with the aid of a strain of the genus Streptomyces.
    Type: Grant
    Filed: April 24, 1989
    Date of Patent: July 31, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Susanne Grabley, Joachim Wink, Carlo Giani, Gerhard Seibert, Wolfgang Raether, Susanne Dobreff, Axel Zeeck
  • Patent number: 4943384
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-groups, and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --Z.sup.o --A-- or --A--Z.sup.o --A.sup.4 --,A is a trans-1,4-cyclohexylene or 1,4-cyclohexenylene group which is unsubstituted or is monosubstituted or polysubstituted in the 2-, 3-, 5- and/or 6-position by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group each of which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, which trans-1,4-cyclohexylene or 1,4-cyclohexenylene group can optionally also be substituted in the 1-position and/or 4-position and one or two CH.sub.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 24, 1990
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
  • Patent number: 4885274
    Abstract: The perfume composition containing 4- (or 5-)-acyl-1,1- (or 3,3-)-[a] compound, which is a novel compound expressed by the formula I, has noble musk fragrance. In addition, this perfume composition has characteristics that it is excellent in both quality and strength of the fragrance, of high safety and capable of being manufactured with low costs.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: December 5, 1989
    Assignee: Takasago Perfumery Co., Ltd.
    Inventors: Nobuo Yamada, Toyohiko Kobayashi
  • Patent number: 4876381
    Abstract: The invention relates to a compound of the formula (II) ##STR1## and the corresponding isomers and salts, in which formula: a and b are integers which independently of one another can assume the values 0 or 1,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent, independently, a hydrogen atom, a linear or branched C.sub.1 -C.sub.6 -alkyl radical or a C.sub.1 -C.sub.4 -alkoxy radical,R.sub.6 represents a C.sub.1 -C.sub.6 -alkyl radical,R.sub.5 and R.sub.12 represent a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl radical, with the proviso that R.sub.5 cannot represent hydrogen if a=b=0 andR.sub.11 has various meanings.These compounds have useful dermatological properties.
    Type: Grant
    Filed: August 18, 1987
    Date of Patent: October 24, 1989
    Assignee: L'Oreal
    Inventors: Gerard Lang, Jean Maignan, Serge Forestier, Serge Restle, Alain Lagrange, Braham Shroot
  • Patent number: 4874891
    Abstract: Compounds of the formula: ##STR1## and the pharmaceutically acceptable esters thereof, wherein rings A and B are selected from the group consisting of ##STR2## wherein x represents an aromatic ring, or the presence or absence of 0, 1, or 2 conjugated or unconjugated .pi. bond(s), andwherein x represents the presence or absence of 0, 1, or 2 conjugated or unconjugated .pi. bond(s), andwherein a non-aromatic .pi. bond, if present, may optionally be converted to an epoxide;and wherein the dotted line represents the presence or absence of a .pi. bond,and wherein:R.sup.1 is H, acyl(1-6), or alkyl(1-6);R.sup.2 is H, alkyl(1.varies.6), 2-propynyl, or allenyl;R.sup.3 and R.sup.4 is each independently H or OR.sup.5, wherein R.sup.5 is H, acyl(1-6), or alkyl(1-6); andwherein R.sub.1 and R.sub.2 is each independently H, alkyl(1-6) or is --C.tbd.CR.sub.3, --CH.dbd.CHR.sub.3, or --CH.dbd.C.dbd.CHR.sub.3, wherein R.sub.3 is selected from the group consisting of H, halo, CF.sub.
    Type: Grant
    Filed: May 1, 1986
    Date of Patent: October 17, 1989
    Assignee: Washington University
    Inventors: Douglas F. Covey, Ricahrd J. Auchus
  • Patent number: 4871877
    Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts and a proton source. The reaction--which is conducted, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substitutes are a perfluoroalkyl group and a hydroxyl group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.
    Type: Grant
    Filed: May 20, 1988
    Date of Patent: October 3, 1989
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4853151
    Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankfter Haftung
    Inventors: Fritz Vogtle, Wolfgang Calaminus
  • Patent number: 4812409
    Abstract: Hydrolyzable substrates comprise blocked dye moieties which, when cleaved from the substrate during hydrolysis, provide fluorescent dyes having maximum absorptions above about 530 nm and maximum emissions at least about 580 nm at physiological pH. These substrates can be used in analytical determinations of hydrolytic substances including hydrolytic enzymes or biological cells containing such enzymes.
    Type: Grant
    Filed: January 31, 1986
    Date of Patent: March 14, 1989
    Assignee: Eastman Kodak Company
    Inventors: Bruce E. Babb, Robert T. Belly, Patricia M. Scensny
  • Patent number: 4803161
    Abstract: Certain phenalenone and benzphenalenone fluorescent compounds are useful in biomedical studies and analytical determinations. These compounds are particularly useful in assays for living organisms, e.g. microorganisms, carried out at a pH of 9 or less. For these determinations, the compounds can be attached to reducible compounds which will subsequently release the fluorescent moiety upon reduction. In the presence of an electron transfer agent, the reducible compounds are easily reduced by a microorganism.
    Type: Grant
    Filed: January 31, 1986
    Date of Patent: February 7, 1989
    Assignee: Eastman Kodak Company
    Inventors: Bruce E. Babb, Robert T. Belly, Albert J. Mura
  • Patent number: 4749804
    Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: June 7, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: George C. Schloemer
  • Patent number: 4731468
    Abstract: The present invention relates to new aglycons which correspond to the general formula: ##STR1## in which: R.sub.1, R.sub.2, R.sub.3 and R.sub.5, which can be identical or different, represent a hydrogen atom or a group OH, OMetal or OR.sub.4, R.sub.4 being a substituted or unsubstituted C.sub.1 to C.sub.6 alkyl group,R represents a hydrogen atom or a group COCH.sub.2 R', R' being hydrogen or an alkyl, hydroxyl, alkoxy or aryl group,R.sub.6 and R.sub.7, which are always different, represent either a hydrogen atom or an OH group, andR.sub.8 represents a hydrogen atom or the group CH.sub.3 CO--.Application to the preparation of antibiotics and antitumoral agents.
    Type: Grant
    Filed: August 29, 1984
    Date of Patent: March 15, 1988
    Assignee: Laboratoires Hoechst S.A.
    Inventors: Jean-Pierre Gesson, Martine Mondon, Abdallah A. Abdallah, Jean-Claude Jacquesy, Patricia Petit nee Monpontet
  • Patent number: 4710584
    Abstract: New derivatives of 3-benzylidene camphor, process for preparing them and their use as protective agents against UV rays and as medicaments.Derivatives of 3-benzylidene camphor of formula: ##STR1## in which R denotes a hydrogen atom, a methyl or ethyl radical,R' denotes a hydrogen atom, a methyl or ethyl radical,R and R' being unable simultaneously to denote a hydrogen atom,R.sub.1 denotes a --COOR.sub.2, --CONHR.sub.2, --COO.sup.- M.sup.+, --CHO, --CH(OR.sub.4).sub.2 or --CH.sub.2 OR.sub.4 group,R.sub.2 being an alkyl, alkenyl, cycloalkyl or aralkyl radical containing at most 20 carbon atoms, optionally substituted by hydroxy, alkoxy, amine or quaternary ammonium groups,M denoting a hydrogen atom, an alkali metal or a N.sup.+ (R.sub.3).sub.4 group, R.sub.3 being a hydrogen atom or a C.sub.1 to C.sub.4 alkyl or hydroxyalkyl radical,R.sub.4 denoting H, alkyl, cycloalkyl or aralkyl containing at most 20 carbon atoms.Application in cosmetics for protection against UV rays.
    Type: Grant
    Filed: December 11, 1984
    Date of Patent: December 1, 1987
    Assignee: L'Oreal
    Inventors: Gerard Lang, Serge Forestier, Alain LaGrange
  • Patent number: 4691059
    Abstract: This invention describes UV-stabilized step growth polymers such as polyesters, polyurethanes, polycarbonates, and combinations thereof. The UV-stabilizing moieties present in these polymers comprise chemically bound, pendant ortho-hydroxydiphenyl ketone based moieties. The polymers are especially useful as protective films and fibers which are highly resistant to ultraviolet (UV) and sunlight degradation.
    Type: Grant
    Filed: August 30, 1985
    Date of Patent: September 1, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Sumita B. Mitra, Smarajit Mitra
  • Patent number: 4675341
    Abstract: The invention relates to novel [(5,6-dichloro-3-oxo-9a-propyl-2,3,9,9a-tetrahydrofluoren-7-yl)oxy]ethanol , its derivatives, and their salts. The compounds are useful for the treatment and prevention of injury to the brain and of edema due to head trauma, stroke (particularly ischemic), arrested breathing, cardiac arrest, Reye's syndrome, cerebral thrombosis, cerebral embolism, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections including that due to AIDS virus, various brain concussions and elevated intracranial pressure.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: June 23, 1987
    Assignee: Merck & Co., Inc.
    Inventor: Edward J. Cragoe, Jr.
  • Patent number: 4656192
    Abstract: New tropolone derivatives of the general formula: ##STR1## wherein R.sup.1 represents H or an alkyl group, R.sup.2 represents an alkyl, aryl, aralkyl or heterocyclic group and R.sup.3 represents an alkoxyl, aryl or heterocyclic group or a group of the formula: ##STR2## or R.sup.2 and R.sup.3 may form together a part of a heterocyclic group, their metal complex salts, processes for the preparation thereof and the use thereof as anti-tumor agents.
    Type: Grant
    Filed: June 14, 1984
    Date of Patent: April 7, 1987
    Assignee: Mect Corporation
    Inventor: Masatoshi Yamato
  • Patent number: 4642373
    Abstract: 1,2,3,4,4a,4b,5,6,7,8,8a,12b-Dodecahydro-7-(oxo, hydroxy or amino)-9-hydroxy-11-(alkyl, alkoxy or alkoxyalkyl)triphenylenes, 2,3,3a,3b,4,5,6,7,7a,11b-decahydro-6-(oxo, hydroxy or amino)-8-hydroxy-10-(alkyl, alkoxy or alkoxyalkyl)-1H-cyclopenta[1]-phenanthrenes, 2,3,4,4a,4b,5,6,7,8,8a-decahydro-7-(oxo, hydroxy or amino)-9-hydroxy-11-(alkyl, alkoxy, alkoxyalkyl, aralkyl, aralkoxy, aryloxyalkyl or aralkoxyalkyl)-1H-pyrido[1,2-f]phenanthridines, and 1,2,3,3a,3b,4,5,6,7,7a-decahydro-6-(oxo, hydroxy or amino)-8-hydroxy-10-(alkyl, alkoxy or alkoxyalkyl)pyrrolo[1,2-f]phenanthridines and derivatives are valuable as central nervous system active agents or as intermediates to compounds having such activity.
    Type: Grant
    Filed: July 6, 1984
    Date of Patent: February 10, 1987
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4638095
    Abstract: This disclosure describes the extraction of a novel antioxidant, Rosmaridiphenol, isolated from the leaves of Rosemary.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: January 20, 1987
    Assignee: Research Corporation
    Inventors: Stephen S. Chang, Chi-Tang Ho, Christopher M. Houlihan
  • Patent number: 4605761
    Abstract: An improved method for the direct preparation of an enantiomer of a substituted fluorenyloxyacetic acid including the enhancement of a chiral phase transfer alkylation step in the synthesis using a non-ionic surfactant as co-catalyst. The substituted fluorenyloxyacetic acid is useful in the treatment of brain edema.
    Type: Grant
    Filed: December 6, 1985
    Date of Patent: August 12, 1986
    Assignee: Merck & Co., Inc.
    Inventor: Ulf H. Dolling
  • Patent number: 4603223
    Abstract: A novel process for the manufacture of quinone derivatives is described.In this process a compound of the formula ##STR1## is reacted with a compound of the formula ##STR2## and the resulting compound of the formula ##STR3## is subjected to a retro-Diels-Alder reaction. The substituents R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the significance given in the description.
    Type: Grant
    Filed: July 24, 1984
    Date of Patent: July 29, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: August Ruttimann, George H. Buchi
  • Patent number: 4601853
    Abstract: The novel complex of the formula I ##STR1## is an organic material with a high electrical conductivity and with a metallic phase transition at about 125.degree. K. under normal pressure, at which the conductivity increases suddenly. The complex can be used, for example, as an organic electrical conductor.
    Type: Grant
    Filed: February 4, 1985
    Date of Patent: July 22, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Bruno Hilti, Carl W. Mayer
  • Patent number: 4581377
    Abstract: Compounds of formula I below are useful as anti-inflammatory, analgesic and/or anti-pyretic agents: ##STR1## in which R.sup.1 is hydrogen, nitro, amino, hydroxyl, alkoxy of one to four carbon atoms, alkyl of one to four carbon atoms or halogen; R.sup.2 is hydrogen or alkyl of one to four carbon atoms; is a saturated or unsaturated bond; A is CO, CHOH, C(R.sup.5)OH or CHOCOR.sup.6, where R.sup.5 and R.sup.6 are alkyl of one to four carbon atoms; B is alkyl of one to twelve carbon atoms; and X is H.sub.2 or O.
    Type: Grant
    Filed: November 7, 1984
    Date of Patent: April 8, 1986
    Assignee: Nippon Shinyaku Co., Ltd.
    Inventors: Yoshihisa Shibata, Yoshihiko Yoshimoto
  • Patent number: 4576964
    Abstract: Tricyclic benzo fused compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, wherein n is zero, 1 or 2, and t is 1 or 2; M is CH or N, R.sub.1 is H or certain acyl groups; Q is CO.sub.2 R.sub.4, COR.sub.5, C(OR.sub.7)R.sub.5 R.sub.6, CN, CONR.sub.9 R.sub.10, CH.sub.2 NR.sub.9 R.sub.10, CH.sub.2 NHCOR.sub.11, CH.sub.2 NHSO.sub.2 R.sub.12, 5-tetrazolyl or when n is 1, Q and OR.sub.1 together form a lactone or certain reduced derivatives thereof; and Z is certain alkyl, alkoxy, alkoxyalkyl, aralkyl, aralkoxy, aryloxyalkyl or aralkoxyalkyl groups, are valuable central nervous system active agents, methods for their use, pharmaceutical compositions containing them and certain intermediates therefor.
    Type: Grant
    Filed: June 7, 1984
    Date of Patent: March 18, 1986
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4569944
    Abstract: A non-steroidal anti-inflammatory composition comprising an active anti-inflammatory agent having the formula: ##STR1## The active agent is formulated with a pharmaceutically acceptable carrier for use in the treatment of pain, inflammation and other related symptoms on mammals.
    Type: Grant
    Filed: June 21, 1984
    Date of Patent: February 11, 1986
    Assignee: Warner-Lambert Company
    Inventors: Richard V. Smerbeck, Eugene P. Pittz
  • Patent number: 4556676
    Abstract: Novel trans-isomeric derivatives of 4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine are useful as antidepressant agents. These novel compounds act to block the synaptosomal uptake of norepinephrine and serotonin (5-hydroxy-tryptamine), thereby alleviating abnormalities at central receptor sites. The preferred embodiment is the enantiomer trans-(1R)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalen amine and its pharmaceutically acceptable acid addition salts.
    Type: Grant
    Filed: September 5, 1980
    Date of Patent: December 3, 1985
    Assignee: Pfizer Inc.
    Inventors: Willard M. Welch, Jr., Charles A. Harbert, B. Kenneth Koe, Allen R. Kraska
  • Patent number: 4541948
    Abstract: The invention relates to new polyalkyl indan-1-ones, to processes for manufacturing them and to the use thereof in perfumes. The new products are polyalkyl substituted hydrindacen-1-ones and polyalkyl substituted hexahydro benz(f) inden(1H)-1-ones belonging to the family of substances defined by the following formula: ##STR1## in which R1, R2, R3, R4 are H or an alkyl radical having one to three atoms of carbon and X is a --CHR5-- group or a --CHR5--CHR6-- group in which R5 and R6 are H or CH3 and at least three of the radicals R1, R2, R3, R4, R5 and R6 are alkyl radicals.
    Type: Grant
    Filed: February 28, 1983
    Date of Patent: September 17, 1985
    Assignee: P. Robertet & Cie [Societe Anomyme]
    Inventor: Daniel R. Joulain
  • Patent number: 4529490
    Abstract: Aryliodonium salts resulting from the condensation of aryliodosotosylates and aryl ketones are provided which are used as photoinitiators to effect deep section UV cures. Deep section photopolymerizable organic materials are also provided which can be used as encapsulating agents to encapsulate a wide variety of electronic components.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: July 16, 1985
    Assignee: General Electric Company
    Inventors: James V. Crivello, Julia L. Lee
  • Patent number: 4522754
    Abstract: The novel complex of the formula I ##STR1## can be produced for example by electrochemical oxidation of 2-fluoro-5,6,11,12-tetraselenotetracene in the presence of an inert organic solvent and a bromide-containing electrolyte. The novel 2-fluoro-5,6,11,12-tetraselenotetracene can for its part be produced by reacting 2,3-naphthalenedicarboxylic anhydride, in the presence of a Friedel-Crafts catalyst, with fluorobenzene to 2-(4-fluorobenzoyl)-naphthalene-3-carboxylic acid; cyclizing this to 2-fluoro-5,12-naphthacenequinone; reducing the 2-fluoro-5,12-naphthacenequinone to 2-fluorotetracene; reacting the 2-fluorotetracene with sulfuryl chloride to 2-fluoro-5,11- or 2-fluoro-6,12-dichlorotetracene; and finally reacting the last-mentioned at elevated temperature with selenium to obtain 2-fluoro-5,6,11,12-tetraselenotetracene. The complex of the formula I is metallically conducting, and is distinguished by a stable metallic phase down to at least 5.degree. K.
    Type: Grant
    Filed: November 2, 1983
    Date of Patent: June 11, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Bruno Hilti, Carl W. Mayer, Grety Rihs
  • Patent number: 4477668
    Abstract: (+)-5-Methyl-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5,10-imine, and its pharmaceutically acceptable salts is useful as an anxiolytic, antidepressant, anticonvulsant, muscle relaxant and in the treatment of mixed anxiety-depression, minimal brain dysfunction and extrapyramidal disorders such as Parkinson's disease. The racemate of the compound is produced by a four-step synthetic process in about 65% yield from 5H-dibenzo[a,d]cyclohepten-5-one.
    Type: Grant
    Filed: September 3, 1982
    Date of Patent: October 16, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Dean R. Bender, Sandor Karady, Theresa Rothauser
  • Patent number: 4456620
    Abstract: D-Homo-4,17-androstadien-3-one is a pharmacologically effective compound having antiandrogenic activity upon topical application. The compound can be prepared from D-homo-5,17-androstadien-3.beta.-ol by oxidation with simultaneous isomerization of the 5(6)-double bond.
    Type: Grant
    Filed: April 13, 1982
    Date of Patent: June 26, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Henry Laurent, Rudolf Wiechert
  • Patent number: 4440943
    Abstract: 3,7-Substituted phenoxiodinin-5-ium compounds are effective against a variety of aerobic and anaerobic bacteria as well as fungi. The compounds of this invention may be prepared by the direct iodination of a suitably substituted diphenyl ether with iodosyl sulfate in concentrated sulfuric acid. The resulting bisulfate anion may be exchanged with a desired anion by standard metathetic processes.
    Type: Grant
    Filed: March 15, 1982
    Date of Patent: April 3, 1984
    Assignee: The Dow Chemical Company
    Inventor: Edward E. Flagg
  • Patent number: 4438272
    Abstract: Tetracyclic spiro-hydantoin derivatives useful in the treatment of complications arising from diabetes mellitus.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: March 20, 1984
    Assignee: Alcon Laboratories, Inc.
    Inventor: Billie M. York, Jr.
  • Patent number: 4390721
    Abstract: A novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described which can be alkylated stereospecifically to give a 5-endo-protected hydroxyl-bicyclo[2,2,1]heptan-2-one which may then be converted via a sequence of reactions into prostaglandins of the F-series having a protecting group at the 9-position. The synthesis of the tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is also described.
    Type: Grant
    Filed: November 1, 1978
    Date of Patent: June 28, 1983
    Assignee: Allen & Hanburys Limited
    Inventor: Stanley M. Roberts
  • Patent number: 4374984
    Abstract: Compounds of the formula ##STR1## wherein the substituents A, Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4, X, n and m are defined hereinbeloware effective photoinitiators, especially for the photopolymerization of ethylenically unsaturated compounds and for the curing of printing inks.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: February 22, 1983
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Jurgen Eichler, Claus Herz, Karl-Heinz Neisius, Gregor Wehner
  • Patent number: 4332810
    Abstract: Novel N-(substituted) derivatives of 2,5-ethano-8-hydroxy (or methoxy)-1,2,3,4,5,6-hexahydro-3 (or 4)-benzazocine of the formula: ##STR1## are centrally acting analgesics effective in the relief of pain.
    Type: Grant
    Filed: January 26, 1981
    Date of Patent: June 1, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Patrice C. Belanger, Robert N. Young
  • Patent number: 4327036
    Abstract: Process for nuclear chlorination of non-phenolic aromatic compounds, said process comprising contacting and reacting a non-phenolic aromatic compound having a net Hammett .sigma. value of about -0.1 to about 2.0 with chlorine monoxide in the presence of at least one-half an equivalent amount, based on the chlorine monoxide, of an acid having a pK.sub.a no greater than that of trichloroacetic acid, provided, however, when the net Hammett .sigma. value is about 0.7 to about 2.0, the acid has a pK.sub.a no greater than that of trifluoroacetic acid.
    Type: Grant
    Filed: May 8, 1980
    Date of Patent: April 27, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank D. Marsh
  • Patent number: 4298535
    Abstract: There is presented a synthetic process for the production of anthracyclinones, the aglycones of the anthracyclines. Also disclosed are novel intermediates in the above process. The end product aglycones may thereafter be utilized to produce biologically useful products such as carminomycin or adriamycin.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: November 3, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Pierre Vogel, Pierre-Alain Carrupt
  • Patent number: 4284819
    Abstract: Processes and compositions are described for the use in foodstuff flavor and aroma, tobacco flavor and aroma and perfume and perfumed article aroma augmenting, modifying, altering and enhancing compositions and as foodstuff, chewing gum, toothpaste, medicinal product, tobacco, perfume and perfumed article aroma imparting materials of acetyl hydrindacenes and acetyl indanes and mixtures of same, said acetyl indanes and acetyl hydrindacenes having the structures: ##STR1## and existing in the liquid phase at ambient temperature and pressure.
    Type: Grant
    Filed: June 5, 1980
    Date of Patent: August 18, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Manfred H. Vock, Frederick L. Schmitt, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4282354
    Abstract: In general, materials having the structure ##STR1## wherein A represents phenylene, napthylene, anthracenediyl, and dibenzothien-diyl;R.sub.1 and R.sub.2, which may be the same or different when taken alone represent hydrogen, cyano, alkylcarbonyl and arylcarbamoyl, arylcarbonyl, cyanoaryl;R.sub.1 and R.sub.2, when taken together, represent sufficient atoms to form substituted and unsubstituted radicals selected from the group consisting of furanylidene, fluorenylidene, pyrimidinylidene, thiazolidinylidene, pyrrolinyl, and indenyl, isoxazolinylidene, pyrazolinylidene and indanylidene, wherein said substituents are selected from the group consisting of hydrogen, cyano, aryl, oxo, thioxo, nitro, alkyl, nitroaryl, carbamoyl and cyanoalkyl; andalkyl represents an alkyl group having from one to six carbon atoms; aryl represents an aromatic nucleus selected from the group consisting of benzene, napthalene or anthracene, are useful in electrophoretic migration imaging processes.
    Type: Grant
    Filed: April 18, 1979
    Date of Patent: August 4, 1981
    Assignee: Eastman Kodak Company
    Inventors: James A. Van Allan, Louis J. Rossi, Melvin S. Bloom, Michael T. Regan, Hal E. Wright, Joseph Y. Kaukeinen
  • Patent number: 4277631
    Abstract: A novel norpatchoulenol synthesis is disclosed. The key step in the synthesis is an intramolecular Diels-Alder condensation of a trisubstituted silyloxy derivative of cyclohexadienone. Novel intermediates, namely trisubstituted silyloxy methanonaphthalenes (Formula V, infra) and trisubstituted silyloxy cyclohexadienes (Formula IV, infra) are also disclosed.
    Type: Grant
    Filed: August 6, 1979
    Date of Patent: July 7, 1981
    Assignee: Givaudan Corporation
    Inventor: Wolfgang Oppolzer
  • Patent number: 4268692
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n -wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: May 19, 1981
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4268523
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n - wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: May 19, 1981
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4260511
    Abstract: Described for use in augmenting or enhancing the aroma of solid or liquid anionic, cationic or nonionic detergents are acetyl hydrindacenes and acetyl indanes and mixtures of same.
    Type: Grant
    Filed: June 5, 1980
    Date of Patent: April 7, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Manfred H. Vock, Frederick L. Schmitt, Joaquin Vinals, Jacob Kiwala
  • Patent number: 4247484
    Abstract: Novel keto-diphenol compounds are disclosed. These compounds are intermediates in the production of novel tetraphenolic compounds which have utility as branching agents in the production of novel, randomly branched polycarbonates.
    Type: Grant
    Filed: September 20, 1979
    Date of Patent: January 27, 1981
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4215044
    Abstract: Process for preparing an organic compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40.degree. C. to -100.degree. C., ROF and ##STR1## R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF.sub.2 ; R.sup.1 is hydrocarbyl of 1-6 carbon atoms;each R.sup.2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms;R.sup.3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R.sup.1).sub.3, OH, NH.sub.2, alkoxy of 1-6 carbon atoms, aryloxy, NHR.sup.1 and NR.sup.1.sub.2 wherein R.sup.1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms;R.sup.3 and one R.sup.2 taken together is a diradical which with the C.dbd.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: July 29, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William J. Middleton
  • Patent number: 4209543
    Abstract: Processes and compositions are described for the use in foodstuff flavor and aroma, tobacco flavor and aroma and perfume and perfumed article aroma augmenting, modifying, altering and enhancing compositions and as foodstuff, chewing gum, toothpaste, medicinal product, tobacco, perfume and perfumed article aroma imparting materials of acetyl hydrindacenes and acetyl indanes and mixtures of same, said acetyl indanes and acetyl hydrindacenes having the structures: ##STR1## and existing in the liquid phase at ambient temperature and pressure.
    Type: Grant
    Filed: October 20, 1978
    Date of Patent: June 24, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Manfred H. Vock, Frederick L. Schmitt, Joaquin Vinals, Jacob Kiwala