Polycyclo Ring System Patents (Class 568/439)
  • Publication number: 20130315841
    Abstract: Methods for the synthesis and use of functionalized, substituted naphthalenes are described. The functionalized, substituted naphthalenes display useful properties including liquid crystals and fluorescence properties, such as solvatochromatic fluorescence, with high quantum yields, Stoke's shift, and show emission maxima that are significantly red-shifted.
    Type: Application
    Filed: March 15, 2013
    Publication date: November 28, 2013
    Inventor: Kay M. Brummond
  • Publication number: 20120251449
    Abstract: The present invention claims fluoro- & iodo-containing aldehydes as ALDH substrates for use as diagnostic imaging agents or as therapeutic agents. The aldehydes are both directly and indirectly attached to an aromatic or a straight chain ring. ALDH activity was monitored either by the formation of acid-product or consumption of aldehyde substrates.
    Type: Application
    Filed: December 22, 2010
    Publication date: October 4, 2012
    Inventors: Vijaya Raj Kuniyil Kulangara, Alan Cuthbertson, Peter Iveson, Chitralekha Rangaswamy, Veena Rao, Rajiv Bhalla
  • Publication number: 20120251492
    Abstract: Provided are a triterpene derivative represented by a general formula (I), a pharmaceutically acceptable salt thereof, and an agent for preventing or treating chronic hepatitis C comprising the triterpene derivative or the salt as an active ingredient: [in the formula (I), R1 represents a carboxyl group, a hydroxymethyl group, —CH2OSO3H, or and R2 represents —OR3 or —O— (CH2) m-OR4, where R3 represents a benzyl group which may be substituted with a hydroxymethyl group, a dimethylaminomethyl group, a phenylaminomethyl group, a morpholinomethyl group, a carboxyl group, or a formyl group, a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, or a hydroxy C1-6 alkyl group, R4 represents a phenyl group which may be substituted with a carboxyl group, and m represents an integer of 1 to 3, with the proviso that a case where R1 is —CH2OH, and R3 is a C1-6 alkyl group, a C2-6 alkenyl group, or a benzyl group is excluded].
    Type: Application
    Filed: December 15, 2010
    Publication date: October 4, 2012
    Applicant: MEIJI SEIKA PHARMA CO., LTD.
    Inventors: Makoto Ishikawa, Shigeki Suzuki, Makoto Aoki, Nobuto Minowa, Kokichi Suzuki
  • Publication number: 20110021613
    Abstract: Compounds obtainable from plants, e.g. of the genus Eucalyptus, or from microorganisms are shown to be useful as CNS activity modulators useful e.g. in the treatment of depression, for lifting mood and/or for increasing behavioural initiative and the like. This use and related aspects form embodiments of the invention. Also compounds as such are presented. The compounds useful are acylphloroglucine derivatives of the formula I, wherein the substituents are as defined in the description.
    Type: Application
    Filed: December 11, 2007
    Publication date: January 27, 2011
    Applicant: INTERMED DISCOVERY GMBH
    Inventors: Ernst Roemer, Torsten Grothe
  • Patent number: 7777081
    Abstract: A process for effectively producing a 4-(4-alkylcyclohexyl)benzaldehyde, 4-(cyclohexyl)benzaldehyde, a 4-(trans-4-alkylcyclohexyl)benzaldehyde and a (trans-4-alkylcyclohexyl)benzene useful for electronic material applications such as liquid crystals and for pharmaceutical and agrochemical applications, etc., are disclosed. The present invention provides (1) a process for producing a 4-(4-alkylcyclohexyl)benzaldehyde or 4-(cyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene or cyclohexylbenzene with carbon monoxide, (2) a process for producing a 4-(trans-4-alkylcyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene having a cis/trans molar ratio of 0.3 or less with carbon monoxide, and (3) a process for producing a (trans-4-alkylcyclohexyl)benzene by isomerizing a mixture of the cis and trans isomers of a (4-alkylcyclohexyl)benzene, all of the processes being performed in the presence of HF and BF3.
    Type: Grant
    Filed: May 8, 2007
    Date of Patent: August 17, 2010
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Mitsuharu Kitamura, Junya Nishiuchi, Norio Fushimi
  • Publication number: 20100071769
    Abstract: Disclosed is a novel fluorene derivative and an organic electronic device using the same. The organic electronic device has excellent efficiency, driving voltage, and a lifespan.
    Type: Application
    Filed: December 6, 2007
    Publication date: March 25, 2010
    Inventors: Jae-Soon Bae, Dong-Hoon Lee, Dae-Woong Lee, Sung-Ku Hong, Hyun Nam, Chang-Hwan Kim
  • Publication number: 20090299078
    Abstract: Disclosed are several different processes that can be utilized to prepare endohedral metallofullerenes with specific characteristics. Processes can be utilized to prepare monoadducts including cycloaddition of functional groups to the [6,6] double bond of a pyrene-type site of the fullerene. Also disclosed are simple, economical methods for separating fullerene isomers based upon the different oxidation potentials of the isomers.
    Type: Application
    Filed: February 27, 2007
    Publication date: December 3, 2009
    Inventor: Luis Echegoyen
  • Publication number: 20090072712
    Abstract: The present invention relates to the improvement of organic electronic devices, in particular electroluminescent devices, by using compounds which can have a plurality of isomers, where one of these isomers is present in excess.
    Type: Application
    Filed: November 3, 2005
    Publication date: March 19, 2009
    Inventors: Philipp Stoessel, Esther Breuning, Horst Vestweber, Holger Heil
  • Patent number: 7470821
    Abstract: The invention relates to novel aldolase-inhibiting compounds that can be advantageously used as medicaments (in therapeutic doses), especially for treating certain cancers, due to the inhibition efficacy thereof. An inventive compound corresponds to general formula (I) wherein the aldehyde group (—CHO) and the phenol group (—OH) are linked to two carbon atoms adjacent to the same aromatic chain, i.e., the first aromatic chain, and R is a phosphate group or a phosphate group mimetic linked to a carbon atom of the second aromatic chain.
    Type: Grant
    Filed: June 29, 2004
    Date of Patent: December 30, 2008
    Assignees: Valorisation-Recherche, Limited Partnership, Universite Paul Sabatier Toulouse III
    Inventors: Chantal Dax, Casimir Blonski, Laurent Azema, Jurgen Sygusch
  • Patent number: 7456323
    Abstract: A new 1,3-bis(3-formyl-4-hydroxyphenyl)adamantane, which provides a material offering excellent properties such as heat resistance and mechanical strength for use as an intermediate material for adamantanebisphenol derivatives or use in photosensitive resist materials, epoxy resins and other synthetic resins, thermosensitive recording materials, and the like, can be obtained through an industrial process in an easy manner at a good yield and high purity by producing a Schiff base from a 1,3-bis(4-hydroxyphenyl)adamantane by causing it to react with a hexamethylenetetramine or other substance in the presence of an acid, and then hydrolyzing the obtained Schiff base using an acid. A new polynuclear polyphenol is also provided that may be derived from the same.
    Type: Grant
    Filed: June 13, 2006
    Date of Patent: November 25, 2008
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Akira Yoshitomo, Tatsuya Iwai, Kentaro Watanabe
  • Publication number: 20080242896
    Abstract: A new 1,3-bis(3-formyl-4-hydroxyphenyl)adamantane, which provides a material offering excellent properties such as heat resistance and mechanical strength for use as an intermediate material for adamantanebisphenol derivatives or use in photosensitive resist materials, epoxy resins and other synthetic resins, thermosensitive recording materials, and the like, can be obtained through an industrial process in an easy manner at a good yield and high purity by producing a Schiff base from a 1,3-bis(4-hydroxyphenyl)adamantane by causing it to react with a hexamethylenetetramine or other substance in the presence of an acid, and then hydrolyzing the obtained Schiff base using an acid. A new polynuclear polyphenol is also provided that may be derived from the same.
    Type: Application
    Filed: June 13, 2006
    Publication date: October 2, 2008
    Applicant: Honshu Chemical Industry Co., Ltd.
    Inventors: Akira Yoshitomo, Tatsuya Iwai, Kentaro Watanabe
  • Publication number: 20080145708
    Abstract: The present invention relates to the improvement of organic electroluminescent devices, in particular blue-emitting devices, by using compounds of the formula (1) as dopants in the emitting layer.
    Type: Application
    Filed: March 20, 2006
    Publication date: June 19, 2008
    Applicant: Merck Patent GmbH
    Inventors: Holger Heil, Philip Stoessel, Horst Vestweber, Rocco Fortte
  • Patent number: 6756497
    Abstract: Benzoic acid derivatives useful as intermediates for the preparation of drugs and agricultural chemicals, particularly compounds having herbicidal activity; and easy and economical processes for the preparation of the same. The processes are specifically those represented by reaction formula for the preparation of compounds represented by general formulae (1) and (6).
    Type: Grant
    Filed: January 12, 2001
    Date of Patent: June 29, 2004
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Yuuki Nakagawa, Masao Yamaguchi, Hiroyuki Adachi, Hiroyuki Yamanaka, Tomio Yagihara, Masami Hatano
  • Publication number: 20040006235
    Abstract: In a process for the preparation of ring compounds via a combinatorial synthesis, the reaction procedure is based on a Suzuki coupling, subsequent halo-demetallation and finally a further Suzuki coupling. The Suzuki couplings are each carried out with a boronic acid or a boronic acid ester. The reaction procedure uses provides novel ring compounds and uses novel synthesis units used for this purpose. The novel ring compounds are suitable for use as constituents in liquid-crystalline mixtures.
    Type: Application
    Filed: March 17, 2003
    Publication date: January 8, 2004
    Applicant: Merck Patent GmbH
    Inventors: Detlef Pauluth, Peer Kirsch, Peter Baeuerle, Oliver Deeg
  • Patent number: 6630607
    Abstract: Aromatic methylidene compounds of the following general formula wherein R11 and R21 independently in each occurrence represent an unsubstituted or substituted alkyl or alkoxy group, a halogen, a cyano group or a nitro group, n11 and n21 are, respectively, an integer, R31 and R41 independently represent hydrogen, an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted aromatic group, or an unsubstituted or substituted aromatic heterocyclic group and may join to complete a condensed ring, along with other types of aromatic methylidene compounds wherein the moieties attached to the naphthalene ring are attached to different positions of the ring. The preparation of the methylidene compounds is also described along with intermediate compounds and their preparation.
    Type: Grant
    Filed: January 24, 2002
    Date of Patent: October 7, 2003
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventor: Mitsuru Hashimoto
  • Patent number: 6420610
    Abstract: Aromatic aldehyde compounds of formula (4) and (6) are disclosed, wherein Y is a methylene group with various substitutions and R represents various substituents.
    Type: Grant
    Filed: September 13, 2000
    Date of Patent: July 16, 2002
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Takashi Nakamura, Toshiyuki Makuta, Koki Nakamura
  • Patent number: 6084134
    Abstract: 9-Anthracenecarbaldehydes are obtained in a particularly advantageous manner by reacting the corresponding anthracene derivatives with dimethylformamide in the presence of phosphoryl chloride, hydrolyzing the resulting reaction mixture and precipitating the 9-anthracenecarbaldehyde that is formed by admixing a base.
    Type: Grant
    Filed: March 27, 1998
    Date of Patent: July 4, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wolfram Eichinger
  • Patent number: 6043397
    Abstract: A method for the production of a fluorine-containing aromatic compound is provided which allows the relevant reaction to proceed in a standard reaction vessel such as, for example, a glass vessel at room temperature under an ambient pressure without requiring provision of such special devices as have been necessary heretofore or adoption of harsh reaction conditions. This method comprises causing an aromatic compound (A) having a cyclic skeletal part of 6 to 16 carbon atoms containing a plurality of --C(.dbd.O)X groups, wherein X stands for a hydrogen atom, a halogen atom, or an alkyl group of 1 to 10 carbon atoms, and having the remaining hydrogen atoms unsubstituted or partly or wholly substituted with at least one species of halogen atom to react with a compound (B) represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently stand for an alkyl group of 1 to 6 carbon atoms or a phenyl group.
    Type: Grant
    Filed: August 25, 1998
    Date of Patent: March 28, 2000
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Seiichi Teshima, Yoshinobu Asako
  • Patent number: 5780675
    Abstract: The invention provides deoxygossylic compounds having useful biological activities, and methods for the synthesis of these and related compounds. The invention further provides valuable intermediates for the synthesis of the compounds, and pharmaceutical compositions containing biologically active compounds according to the invention.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: July 14, 1998
    Assignee: The University of New Mexico
    Inventors: Robert D. Royer, Lorraine M. Deck, David L. VanderJagt
  • Patent number: 5574036
    Abstract: Novel pharmaceutically/cosmetically-active adamantyl-substituted polycyclic acetylene compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(f): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: November 12, 1996
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Bruno Charpenter
  • Patent number: 5457239
    Abstract: A process for the preparation of a formylated aromatic compound comprising contacting an aromatic compound with (i) a halogenated compound in the presence of a Lewis acid, and (ii) a base, is described. The subject process provides an efficient and effective means of preparing formylated compounds which may be useful in a wide variety of applications.
    Type: Grant
    Filed: May 25, 1994
    Date of Patent: October 10, 1995
    Assignee: Union Camp Corporation
    Inventors: Walter C. Frank, Richard L. Veazey, John J. Mahurter, Mark J. Jenkins, Neil R. Fairfax
  • Patent number: 5326898
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, halogen or lower alkoxy of 1 to 6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1 to 6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 2 to 10 carbons, cyclo or branch-chained alkyl of 3 to 10 carbons, and straight chain alkenyl having 2 to 10 carbons, or cyclo or branched chained alkenyl of 3 to 10 carbons, and the Z-Y substituent is in a 1,2 (ortho) or 1,3 (meta) position on the phenyl ring relative to the ethene moiety; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: July 5, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5290817
    Abstract: The invention relates to benzylindane phospholipase A.sub.2 inhibitors, pharmaceutical compositions containing them, and methods of treating phospholipase A.sub.2 -mediated conditions in mammals by administration of a therapeutically effective amount of such a benzylindane phospholipase A.sub.
    Type: Grant
    Filed: June 9, 1992
    Date of Patent: March 1, 1994
    Assignee: The Du Pont Merck Pharmaceutical Co.
    Inventor: Joseph J. Petraitis
  • Patent number: 5162588
    Abstract: Compound of formula ##STR1## wherein a) indexes m and n are identical and stand each for an integer number equal to zero, symbols R.sup.1 and R.sup.2 are identical and represent each a hydrogen atom, or are different and represent each a hydrogen atom or a methyl radical, symbols R.sup.5 and R.sup.8 stand each for a methyl radical, symbols R.sup.6 and R.sup.7 can be identical or different and designate each a hydrogen atom or a methyl radical and, either symbol R.sup.4 represents a methyl radical and symbol R.sup.3 stands for a hydrogen atom or a methyl radical, or symbols R.sup.3 and R.sup.4 represent each a methylene radical belonging to a ring such as indicated by the dotted line, with the proviso that the following combinations are excluded:1. R.sup.1 =R.sup.2 =R.sup.3 =R.sup.6 =R.sup.7 =H, or2. R.sup.1 =R.sup.2 =R.sup.3 =H and R.sup.6 or R.sup.7 =CH.sub.3, or3. R.sup.2 =CH.sub.3 and R.sup.3 =R.sup.6 =R.sup.7 =H, or4. R.sup.2 =CH.sub.3 and R.sup.3 =H and R.sup.6 or R.sup.7 =CH.sub.3, or5. R.sup.1 =R.sup.
    Type: Grant
    Filed: June 26, 1990
    Date of Patent: November 10, 1992
    Assignee: Firmenich S.A.
    Inventors: Charles Fehr, Jose Galindo
  • Patent number: 5089635
    Abstract: 13-alkyl-11.beta.-phenyl-gonanes of general formula I ##STR1## wherein A and B together stand for an oxygen atom, a CH.sub.2 group or a second bond between carbon atoms 9 and 10,X is an oxygen atom or the hydroxyimino grouping N.about.OH,R.sub.1 is a straight-chained or branched, saturated or unsaturated alkyl radical with up to 8 carbon atoms, which contains the grouping ##STR2## with X as described above, R.sub.2 is a methyl or ethyl radical in the .alpha. or .beta. position,R.sub.9, R.sub.10, R.sub.11 and R.sub.12 each stand for a hydrogen atom, a hydroxy, alkyl, alkoxy or acyloxy group with 1 to 4 carbon atoms respectively or a halogen atom and R.sub.3 and R.sub.4 have a variety of meanings, have antigestagenic and antiglucocorticoid effects.
    Type: Grant
    Filed: February 7, 1986
    Date of Patent: February 18, 1992
    Assignee: Schering Aktiengesellschaft
    Inventors: Gunter Neef, Sybille Beier, Walter Elger, David Henderson, Eckard Otto, Ralph Rohde
  • 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: 4804785
    Abstract: Alpha,beta-substituted acroleins of the general formula I ##STR1## where A and B are identical or different and are each C.sub.1 -C.sub.4 -alkyl, naphthyl, biphenyl or phenyl which may be monosubstituted or polysubstituted by halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, phenoxy or phenylsulfonyl, are prepared by a process in which a compound of the general formula III ##STR2## where A has the above meanings and R.sup.1 and R.sup.2 are identical or different and are each C.sub.1 -C.sub.4 -alkyl or together possess the carbon atoms required to complete a ring, is reacted with a phosphorus compound of the general formula IV or V ##STR3## where B the meanings stated above, R.sup.1 and R.sup.2 are as defined above and X.sup..crclbar. is a halide ion, in the presence of a base. The alpha,beta-substituted acroleins can be further processed to give hydroxymethyloxiranes.
    Type: Grant
    Filed: September 16, 1987
    Date of Patent: February 14, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Stefan Karbach, Hans-Gert Recker, Marco Thyes
  • Patent number: 4358620
    Abstract: Novel 9-aminoalkyl-methanoanthracenes of the formula: ##STR1## wherein A is C.sub.1 -C.sub.4 alkylene or C.sub.3 -C.sub.4 alkenylene and R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 cycloalkyl(C.sub.1 -C.sub.3)alkyl, ar(C.sub.1 -C.sub.3)alkyl or polyhalo(C.sub.2 -C.sub.4)alkyl or, when taken together with the adjacent nitrogen atom, they may form a 5 to 7-membered nitrogen-containing heterocyclic ring which may contain an additional hetero atom, and their non-toxic salts, which are useful as anti-anxiety, anti-depressant, major tranquilizer, anti-histamine and anti-allergy drugs and can be prepared through a novel key intermediate, i.e. 9-formyl-9,10-dihydro-9,10-methanoanthracene, by various methods.
    Type: Grant
    Filed: April 14, 1980
    Date of Patent: November 9, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Sunagawa, Hiromi Sato, Junki Katsube, Hisao Yamamoto
  • Patent number: 4351950
    Abstract: Novel substituted arylene compounds and methods for their preparation and use are disclosed. These new compounds are useful as anti-arteriosclerotic agents.
    Type: Grant
    Filed: January 2, 1980
    Date of Patent: September 28, 1982
    Assignee: Warner-Lambert Company
    Inventor: Ila Sircar
  • Patent number: 4224344
    Abstract: Novel 9-aminoalkyl-methanoanthracenes of the formula: ##STR1## wherein A is C.sub.1 -C.sub.4 alkylene or C.sub.3 -C.sub.4 alkenylene and R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 cycloalkyl(C.sub.1 -C.sub.3)alkyl, ar(C.sub.1 -C.sub.3)alkyl or polyhalo(C.sub.2 -C.sub.4)alkyl or, when taken together with the adjacent nitrogen atom, they may form a 5 to 7-membered nitrogen-containing heterocyclic ring which may contain an additional hetero atom, and their non-toxic salts, which are useful as anti-anxiety, anti-depressant, major tranquilizer, anti-histamine and anti-allergy drugs and can be prepared through a novel key intermediate, i.e., 9-formyl-9,10-dihydro-9,10-methanoanthracene, by various methods.
    Type: Grant
    Filed: December 11, 1975
    Date of Patent: September 23, 1980
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Sunagawa, Hiromi Sato, Junki Katsube, Hisao Yamamoto