Tricyclo Ring System Patents (Class 562/499)
  • Publication number: 20030018065
    Abstract: This invention provides processes for preparing a group of novel bridged tricyclic compounds having the formula: 1
    Type: Application
    Filed: June 27, 2002
    Publication date: January 23, 2003
    Applicant: Wyeth
    Inventors: Alexander Alexei Greenfield, John Anthony Butera
  • Patent number: 6492422
    Abstract: Tricyclic sulfonamide compounds and derivatives are described as well as methods for the preparation and pharmaceutical compositions of same, which are useful as inhibitors of matrix metalloproteinases, particularly gelatinase A, collagenase-3, and stromelysin-1 and for the treatment of multiple sclerosis, atherosclerotic plaque rupture, aortic aneurysm, heart failure, left ventricular dilation, restenosis, periodontal disease, or other autoimmune or inflammatory disorders dependent upon tissue invasion by leukocytes or other activated migrating cells, acute and chronic neurodegenerative disorders including stroke, head trauma, spinal cord injury, Alzheimer's disease, amyotrophic lateral sclerosis, cerebral amyloid angiopathy, AIDS, Parkinson's disease, Huntington's disease, prion diseases, myasthenia gravis, and Duchenne's muscular dystrophy.
    Type: Grant
    Filed: March 27, 2002
    Date of Patent: December 10, 2002
    Assignee: Warner-Lambert Company
    Inventors: Patrick Michael O'Brien, Joseph Armand Picard, Drago Robert Sliskovic
  • Patent number: 6476258
    Abstract: An industrially advantageous process for producing an aryloxyacetic acid represented by the formula (2): wherein m represents an integer of 1 or 2, n represents an integer from 0 to 4, Ar represents a aromatic hydrocarbon ring, each Rs independently represents an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom, an alkylcarbonyl group, an arylcarbonyl group, a carboxyl group or a nitro group, comprising a step in which an oxygen-containing gas is made act on an aryloxyethanol represented by the formula (1): (R)n-Ar&Parenopenst;O—CH2.CH2.OH)m  (1) wherein m, n, Ar, and R, respectively, have the same meanings as defined above, under conditions of using a catalyst comprising palladium and an indium compound and/or a copper compound in an aqueous medium and in the presence of 0.
    Type: Grant
    Filed: July 5, 2000
    Date of Patent: November 5, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masashi Komatsu, Junichi Ishikawa
  • Patent number: 6448413
    Abstract: The invention relates to a new process for the synthesis of 17&bgr;-hydroxy-17&agr;-methyl-1,3-seco-2-nor-5&agr;-androstane-3-acid derivatives of formula (I) wherein the meaning of Z is carboxyl or formyl group and to the new secoindoxylidene carboxylic acid derivatives of formula (II) wherein R1 and R2 independently are C1-C4 alkyl or alkoxy group, hydrogen or halogen atom—which are intermediates for preparing the compounds of formula (I). The 17&bgr;-hydroxy-17&agr;-methyl-1,3-seco-2-nor-5&agr;-androstane-3-acid derivatives of formula (I) are intermediates in the synthesis of oxandrolon (17&bgr;-hydroxy-17&agr;-methyl-2-oxa-5&agr;-androstane-3-one), which is used as anabolic in therapy.
    Type: Grant
    Filed: November 30, 2001
    Date of Patent: September 10, 2002
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt.
    Inventors: Csaba Santa, Zoltan Tuba, Sandor Maho, Janos Szeles, Gabor Balogh, Janos Brlik, Ferenc Trischler, Gabriella Szilagyi, Erika Bakcsi
  • Publication number: 20020086815
    Abstract: The present invention provides illudin analogs of the general formula I: 1
    Type: Application
    Filed: November 5, 2001
    Publication date: July 4, 2002
    Applicant: The Regents of the University of California
    Inventors: Trevor C. McMorris, Michael J. Kelner
  • Patent number: 6392104
    Abstract: In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the formula (2): wherein R1 and R2 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group; or R1 and R2 may bond together to form a double bond or an aromatic or non-aromatic ring; Y is O or OH and n=1 to 3; or the imide compound and a co-catalyst (e.g., a transition metal compound), an adamantane derivative having a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is oxidized with oxygen. According to the above method, an adamantane derivative having a hydroxyl group together with a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is efficiently obtained.
    Type: Grant
    Filed: November 10, 1998
    Date of Patent: May 21, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano, Naruhisa Hirai
  • Patent number: 6365768
    Abstract: Novel compounds are disclosed that have the chemical structure of Formula (IIB), and its prodrug esters and acid-addition salts, and that are useful as Interleukin-1 and Tumor Necrosis Factor-&agr; modulators, and thus are useful in the treatment of various diseases. wherein the R groups include the following: R1 is selected from the group consisting of hydrogen, a halogen, COOH, C1-C12 carboxylic acids, C1-C12 acyl halides, C1-C12 acyl residues, C1-C12 esters, C1-C12 secondary amides, (C1-C12)(C1-C12) tertiary amides, C1-C12 alcohols, (C1-C12)( C1-C12) ethers, C1-C12 alkyls, C1-C12 substituted alkyls, C2-C12 alkenyls, C2-C12 substituted alkenyls; R2 is selected from hydrogen, a halogen, C1-C12 alkyl, C1-C12 substituted alkyls, C2-C12 alkenyl, C2-C12 substituted alkenyl, C2-C12 alkynyl, and C1-C12 acyl, and C5-C12 aryl.
    Type: Grant
    Filed: May 12, 2000
    Date of Patent: April 2, 2002
    Assignees: Nereus Pharmaceuticals, Inc., University of California
    Inventors: Michael Palladino, Emmanuel A. Theodorakis
  • Patent number: 6020370
    Abstract: Bridged cyclic amino acids of formula ##STR1## are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain and neuropathological disorders. Processes for the preparation and intermediates useful in the preparation are also disclosed.
    Type: Grant
    Filed: May 19, 1998
    Date of Patent: February 1, 2000
    Assignee: Warner-Lambert Company
    Inventors: David Christopher Horwell, Justin S. Bryans, Clare O. Kneen, Andrew I. Morrell, Giles S. Ratcliffe
  • Patent number: 5998471
    Abstract: Compounds of the formula ##STR1## the symbols have the meaning described in the specification.
    Type: Grant
    Filed: August 11, 1998
    Date of Patent: December 7, 1999
    Assignee: Allergan Sales, Inc.
    Inventors: Alan T. Johnson, Min Teng, Vidyasagar Vuligonda, Richard L. Beard, Samuel J. Gillett, Tien T. Duong, Roshantha A. Chandraratna
  • Patent number: 5770763
    Abstract: Novel difunctionalized cyclobutabenzene monomers of the general formula: ##STR1## wherein Z can be hydrogens or a cyclobutane ring; and X and Y are carboxyl, amino, alcohol, isocyanate, acid halide, or bis-acyl halide groups. Exemplary difunctional bitricyclodecatriene monomers are ?2,2'-bidicyclo?2.4.0!octa-1,3,5-triene!-5,5'-dicarboxylic acid (BXTA) and ?2,2'-bitricyclo?6.2.0.0!deca-1,3,(6),7-triene!-7,7'-dicarboxylic acid (QXTA). The difunctionalized bitricyclodecatriene monomers can form part of a polymer backbone chain in which the multiple butane ring functionalities can be easily opened to produce strong, three-dimensional covalent bond crosslinking between polymer chains. The crosslinking can be induced simply by heating the polymer to a temperature in excess of 250.degree. C.
    Type: Grant
    Filed: August 30, 1996
    Date of Patent: June 23, 1998
    Assignee: The Board of Regents of the Univ. of Michigan
    Inventors: David C. Martin, Jeffrey S. Moore, Larry J. Markoski, Kenneth A. Walker, Gary E. Spilman
  • Patent number: 5730903
    Abstract: A thin film comprising a discotic compound having diacetylene groups at the side chain moiety thereof, and a compound represented by formula (1): ##STR1## wherein R.sup.2 represents an alkyl group or an aryl group.
    Type: Grant
    Filed: December 19, 1995
    Date of Patent: March 24, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Masaki Okazaki
  • Patent number: 5723494
    Abstract: Compounds represented by general formula (I) and (II), in which r is 1 or 2, R.sub.2 and R.sub.3 are selected independently from H, CH.sub.3, C.sub.2 H.sub.5 and CHO, provided that R.sub.2 and R.sub.3 are not simultaneously CHO, and in which R.sub.1 is selected from: an aminoalkyl adamantyl group, a monocyclic aminoalkyl group, a dicyclic aminospiro group, a dicyclic amino group (orthofused), a dicyclic amino group, and azacycloalkyl group, an azadicyclic group (orthofused), a dicyclic azaspiro group, and azadicyclic group, and azacycloalkyl group, and a linear or branched aminoalkyl group.
    Type: Grant
    Filed: September 11, 1995
    Date of Patent: March 3, 1998
    Assignee: Rotta Research Laboratorium S.P.A.
    Inventors: Francesco Makovec, Walter Peris, Lucio C. Rovati, Luigi A. Rovati
  • Patent number: 5670696
    Abstract: The invention provides an alicyclic bifunctional compound represented by the formula ##STR1## wherein R is a carboxyl group, a lower alkoxycarbonyl group or a hydroxymethyl group and n is 0 or 1.
    Type: Grant
    Filed: September 1, 1995
    Date of Patent: September 23, 1997
    Assignee: Arakawa Chemical Industires Ltd.
    Inventors: Takaharu Tsuno, Hideki Kobayashi
  • Patent number: 5595996
    Abstract: Compounds of the Formula I ##STR1## wherein: the dotted line indicates that a double bond may be present or absent; R.sup.1 is H, methyl or ethyl; R.sup.2 is .alpha.- or .beta.-C.sub.1-10 straight or branched alkyl; R.sup.3 is CO.sub.2 H, CN, CO.sub.2 R.sup.4, COHNR.sup.4, or CON(R.sup.4).sub.2 ; R.sup.4 is H, C.sub.1-10 straight or branched alkyl, aryl, heteroaryl, or aralkyl; Aryl is phenyl, substituted phenyl, naphthyl, or biphenyl; Heteroaryl is pyridyl, pyrrolyl, thienyl, furanyl or quinolinyl; and Aralkyl is C.sub.1-10 alkyl substituted with one to three phenyl or substituted phenyl moieties; and their pharmaceutically acceptable salts are described. These compounds are 5.alpha.-reductase type 1 inhibitors. They may be used for treating conditions associated with an excess of DHT, either alone or in combination with other 5.alpha.-reductase inhibitors.
    Type: Grant
    Filed: October 25, 1994
    Date of Patent: January 21, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Donald W. Graham, Josephine R. Carlin, Shuet-Hing L. Chiu, Richard L. Tolman
  • Patent number: 5578726
    Abstract: Described is a new process for producing 7.beta.-substituted-4-aza-5.alpha.-androstan-3-ones and related compounds which are 5.alpha.-reductase inhibitors, consisting of reducing the corresponding androsteneone with lithium and liquid ammonia, contacting the product with an isomerizing agent, oxidizing the product to a seco acid and reacting that seco acid with an amine to cyclize to form 4-aza-5.alpha.-androstan-3-ones.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: November 26, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Raman K. Bakshi, Gary H. Rasmusson
  • Patent number: 5576355
    Abstract: A method of inhibiting viruses in which a virus is contacted with diamondoid alcohol, ketone, ketone derivative, adamantyl amino acid, quaternary salt or combinations thereof which have antiviral properties. These diamondoid derivatives are shown to have antiviral activity against HIV.
    Type: Grant
    Filed: December 15, 1993
    Date of Patent: November 19, 1996
    Assignee: Mobil Oil Corp.
    Inventors: Catherine S. H. Chen, Dong-ming Shen
  • Patent number: 5545654
    Abstract: A compound of formula (I), in which each of R.sub.1 and R.sub.2 is independently hydrogen, alkyi or, together with the carbon atom to which it is bonded, a cycloalkyl; and each of R.sub.3 and R.sub.4 is independently hydrogen, alkyl or substituted alkyl. The compounds are useful intermediates and prodrugs.
    Type: Grant
    Filed: January 3, 1994
    Date of Patent: August 13, 1996
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventor: Ingolf Macher
  • Patent number: 5434274
    Abstract: Neuroactive benz[e]indene compounds ##STR1## are prepared by a total synthesis from the following three starting materials ##STR2##
    Type: Grant
    Filed: March 2, 1994
    Date of Patent: July 18, 1995
    Assignee: Washington University
    Inventors: Douglas F. Covey, Yuefei Hu, Mingcheng Han, Charles F. Zorumski
  • Patent number: 5405870
    Abstract: Compounds of formula (Ic): ##STR1## having valuable platelet-aggregation inhibitory activities useful for the prophylaxis and treatment of such diseases as thrombosis and pharmaceutical compositions containing said compounds.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: April 11, 1995
    Assignee: Sankyo Company, Limited
    Inventors: Kazuo Koyama, Shigeo Amemiya, Koichi Kojima, Shinsaku Kobayashi
  • Patent number: 5405978
    Abstract: The present invention is an oxidative process for the conversion of 21-unsaturated progesterones (I) ##STR1## to the corresponding 3,5-secoandrost-5-one-3,17.beta.-dioic acids (II) ##STR2## by use of either ozone or an oxidizing agent, which are useful intermediates in the production of .DELTA..sup.5 -4-aza-17-carbonyl steroids (III) which are useful in production of 5.alpha.-4-aza amide (IV) pharmaceuticals. Also disclosed are the novel 21-unsaturated progesterones (I-C) and 3,5-secoandrost-5-one-3,17.beta.-dioic acids (II-C).
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: April 11, 1995
    Assignee: The Upjohn Company
    Inventor: Paul M. Herrinton
  • Patent number: 5292906
    Abstract: Novel tricyclic steroid analogs are disclosed which are 1H-benz[e]indene dodecahydro compounds that are useful for enhancing GABA-induced chloride currents at the GABA receptor/chloride ionophore complex and can be represented by the following structural formulas: ##STR1## wherein R.sub.1 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl;R.sub.2 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl, in which R.sub.1 and R.sub.2 can be the same or different;R.sub.3 =H or CH.sub.3 ;R.sub.4 =H or CH.sub.3, in which R.sub.3 and R.sub.4 can be the same or different;R.sub.5 =H;R.sub.6 =H;R.sub.5,R.sub.6 =.dbd.O(carbonyl);R.sub.7 =H;R.sub.8 =a hydrogen bond accepting group.R.sub.7,R.sub.8 =.dbd.O(carbonyl); andR'=an ester group.
    Type: Grant
    Filed: January 14, 1993
    Date of Patent: March 8, 1994
    Assignee: Washington University
    Inventors: Douglas F. Covey, Yuefei Hu, Charles F. Zorumski
  • Patent number: 5228898
    Abstract: This invention relates to substituted bicycloheptadione derivatives with high herbicidal activity which are represented by general formula (I) ##STR1## (where R.sup.1 is a lower alkyl group, a phenyl group which may be substituted, an aralkyl group which may be substituted, or a heterocyclic group which may be substituted;R.sup.2 is, same or different, a halogen, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkyl group, an alkoxyalkyl group, or an alkoxylcarbonyl group, and n is 0 to 4;R.sup.3 and R.sup.4 are, same or different, hydrogen or a lower alkyl group).
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: July 20, 1993
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Akiyoshi Ueda, Shigemi Suga, Hiroyuki Adachi, Toshio Aihara, Kazuyuki Tomida, Hideki Yamagishi, Hideo Hosaka
  • Patent number: 5206415
    Abstract: Novel tricyclic steriod analogs are disclosed which are 1H-benz[e]indene dodecahydro compounds that are useful for enhancing GABA-induced chloride currents at the GABA receptor/chloride ionophore complex and can be represented by the following structural formulas: ##STR1## wherein R.sub.1 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl;R.sub.2 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl, in which R.sub.1 and R.sub.2 can be the same or different;R.sub.3 =H or CH.sub.3 ;R.sub.4 =H or CH.sub.3, in which R.sub.3 and R.sub.4 can be the same or different;R.sub.5 =H;R.sub.6 =H;R.sub.5,R.sub.6 =.dbd.O(carbonyl);R.sub.7 =H;R.sub.8 =a hydrogen bond accepting group.R.sub.7,R.sub.8 =.dbd.O(carbonyl); andR'=an ester group.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: April 27, 1993
    Assignee: Washington University
    Inventors: Douglas F. Covey, Yuefei Hu, Charles F. Zorumski
  • Patent number: 5191115
    Abstract: To produce a carboxylic acid R.sup.1 --COOH, in which R.sup.1 is a tertiary branched alkyl residue or a cycloalkyl residue with one or more rings, which may be attached, and possibly substituted by at least one alkyl residue, the alpha carbon atom of the carbonyl group being a tertiary carbon atom, a branched or cyclic alkane R.sup.1 H, in which R.sup.1 is a branched alkyl residue or a cycloalkyl residue with one or more rings, which may be attached, and possibly substituted by at least one alkyl residue, the alpha carbon atom of the hydrogen atom being a tertiary carbon atom or a secondary carbon atom capable of being rearranged during reaction to a tertiary atom, is reacted in the presence of an acid catalyst with a formiate H(CO)O(CR.sup.2 R.sup.3 R.sup.4), in which R.sup.2, R.sup.3 and R.sup.4 denote hydrogen or alkyl, under the three following conditions: that R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: February 5, 1991
    Date of Patent: March 2, 1993
    Assignee: Atochem
    Inventors: Veronique Lazzeri, Roger Gallo, Rachid Jalal
  • Patent number: 4976893
    Abstract: The invention relates to a process for preparing carboxylic acids by platinum-catalyzed oxidation of primary alcohols of limited water solubility with oxygen in a mixture of water and a solubilizer. The solubilizer used is an ether of the general formula R.sub.1 O(CH.sub.2 CH.sub.2 O).sub.n R.sub.2, where n is 1-4 and R.sub.1 and R.sub.2 are alkyl radicals having 1-4 carbon atoms.
    Type: Grant
    Filed: June 18, 1986
    Date of Patent: December 11, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Ernst I. Leupold
  • Patent number: 4973740
    Abstract: A process for producing a tricyclodecanecarboxylic acid ester by reacting dihydrodicyclopentadiene with CO and an alcohol in the presence of anhydrous HF is disclosed. The reaction is performed in a solvent at a temperature of from -20.degree. to 60.degree. C. under a CO partial pressure of from 5 to 50 atm. The alcohol is used in an amount of 0.7 to 5 moles per mole of the dihydrodicyclopentadiene. The anhydrous HF is used in an amount of at least 5 moles per mole of the dihydrodicyclopentadiene. The product tricyclodecanecarboxylic acid ester is useful as a flavor.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: November 27, 1990
    Assignees: Mitsubishi Gas Chemical Co., Inc., Kao Corporation
    Inventors: Masami Ishihara, Takeshi Morokuma
  • Patent number: 4927963
    Abstract: A process for preparing compounds represented by the formula ##STR1## wherein: X is hydrogen or lower alkoxy;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);n is an integer from 2-4;R.sub.2 is hydrogen or methyl; andR.sub.3 is linear or branched alkyl, ##STR2## --(CH.sub.2).sub.m -phenyl or --CH.sub.2 O-phenyl; in which any phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen, anda is an integer of 0, 1 or 2;b is an integer of 3-7;m is an integer of 0, 1 or 2,as a mixture or separately in a sequence starting from an epoxide represented by the formula ##STR3## and processes for making the novel intermediates.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: May 22, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Keith A. M. Walker, Denis J. Kertesz
  • Patent number: 4921526
    Abstract: Substituted benzoyl-bicycloalkyl-1,1,3-diones and related compounds, intermediates therefor, synthesis thereof, and the use of said diones for the control of weeds.
    Type: Grant
    Filed: November 27, 1987
    Date of Patent: May 1, 1990
    Assignee: Sandoz Ltd.
    Inventors: Shy-Fuh Lee, Gary W. Luehr, Carol R. Scott, Werner Trueb
  • Patent number: 4906769
    Abstract: 3-pentenoates are prepared by isomerization of 2-pentenoates to 3-pentenoates by a process in which the 2-pentenoate is treated with from 0.01 to 0.5 mole of cyclic tertiary amine having a pK.sub.a of >6 per mold of 2-pentenoate at from 50.degree. to 250.degree. C. and the 3-pentenoate is distilled off continuously.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: March 6, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Franz Merger, Hans-Juergen Gosch
  • Patent number: 4777184
    Abstract: Prostaglandin derivatives, and specifically derivatives of isocarbacyclin, have an optionally substituted methylene group as a substituent on the .alpha.-carbon atom of the .alpha.-side chain. They have a variety of physiological effects, notably a strong ability to inhibit blood platelet aggregation and a strong anti-ulcer activity.
    Type: Grant
    Filed: April 29, 1986
    Date of Patent: October 11, 1988
    Assignee: Sankyo Company Limited
    Inventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Nobuyoshi Iwata, Takeshi Oshima
  • Patent number: 4760175
    Abstract: This invention relates to novel sweeteners of the formula: ##STR1## wherein A is hydroxyalkyl containing 1-3 carbon atomsA' is hydrogen or alkyl containing 1-3 carbon atoms;Y is --(CHR.sub.2).sub.n --R.sub.1 or --CHR.sub.3 R.sub.4 ;R.sub.1 is cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl containing up to 7 ring carbon atoms and up to a total of 12 carbon atoms;R.sub.2 is H or alkyl containing 1-4 carbon atoms;R.sub.3 and R.sub.4 are each cycloalkyl containing 3-4 ring carbon atoms;n=0 or 1; andm=0 or 1;and food-acceptable salts thereof.
    Type: Grant
    Filed: May 6, 1985
    Date of Patent: July 26, 1988
    Assignee: General Foods Corporation
    Inventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
  • Patent number: 4683330
    Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: July 28, 1987
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4680307
    Abstract: A compound of the formula: ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group, Y.sup.1 is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or C.sub.1 -C.sub.4 alkyl group), ##STR4## (R.sup.6 is as defined above), ##STR5## R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a shingle linkage to from a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: July 14, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Muraoka, Toshio Nakamura, Akihiko Sugie, Keiichi Ono, Michihiro Yamamoto
  • Patent number: 4668814
    Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: May 26, 1987
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4656307
    Abstract: According to the invention a derivative of brendane is provided. The derivative of brendane is represented by the general formula of: ##STR1## wherein R is a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, and R.sup.1 to R.sup.3 each represent a hydrogen atom or a methyl group. The brendane derivative is prepared by reacting an alkenylnorbornene of the general formula of: ##STR2## wherein R.sup.1 to R.sup.3 each represent a hydrogen atom or a methyl group, with carbon monoxide and an alcohol or water in the presence of a catalyst of Group VIII metal compound of the periodic table.
    Type: Grant
    Filed: July 15, 1985
    Date of Patent: April 7, 1987
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Yoshihiro Kobori, Tetsuya Takezono
  • Patent number: 4602107
    Abstract: An advantageous process for producing tricyclo[5.2.1.0.sup.2,6 ]decane-2-carboxylic acid which is useful as a perfume composition.According to the invention, tricyclo[5.2.1.0.sup.2,6 ]dec-8-yl formate (II) is contacted with an inorganic strongly acidic catalyst to obtain tricyclo[5.2.1.0.sup.2,6 ]decane-2-carboxylic acid (I).
    Type: Grant
    Filed: July 18, 1983
    Date of Patent: July 22, 1986
    Assignee: Kao Corporation
    Inventors: Yoshiaki Fujikura, Naotake Takaishi, Yoshiaki Inamoto
  • Patent number: 4585893
    Abstract: An industrially advantageous process for producing 4-homoisotwistane-3-carboxylic acid.According to the invention, tricyclo[5.2.1.0.sup.2,6 ]dec-8-yl-methylformate (II) is contacted with an inorganic strongly acidic catalyst to obtain 4-homoisotwistane-3-carboxylic acid (I).
    Type: Grant
    Filed: July 18, 1983
    Date of Patent: April 29, 1986
    Assignee: KAO Corporation
    Inventors: Yoshiaki Fujikura, Naotake Takaishi, Yoshiaki Inamoto
  • Patent number: 4582698
    Abstract: The imaging of cardiac infarcts with complexed radioactive metals is improved by employing as the complexing agent a compound of the formula ##STR1## wherein substituents A, B, X and Y are each independently selected from radicals including hydrogen, hydroxyalkyl (wherein the alkyl group contains 2-6 carbon atoms), methylenephosphonic, methylene-, ethylene-, and propylenesulfonic, carboxylic acid radicals (having 2-4 carbon atoms) and the alkali or alkaline earth metal, ammonia and amine salts thereof and wherein at least one A, B, X and Y is methylenephosphonic acid or a salt thereof. In particular Tc-99m complexes have been found useful for imaging damaged cardiac tissue.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: April 15, 1986
    Assignee: The Dow Chemical Company
    Inventors: Jaime Simon, David A. Wilson, Wynn A. Volkert
  • Patent number: 4554360
    Abstract: Provided is a process for converting an aromatic compound to prepare an iodoarene, Ar--I, and an aryl compound which is a compound wherein an unsaturated compound is bonded directly to an aryl group, Ar, which process comprises reacting a diaryliodonium salt represented by general formula (I)[Ar--I.sup..sym. --Ar]X.sup..crclbar. (I)wherein Ar is an aryl group which may be substituted and two Ar's are identical and X.sup..crclbar. is a counter ion inert to the reaction with the unsaturated compound in a solvent in the presence of a transition metal catalyst and a base or a reducing metal, said reaction being carried out at a temperature not higher than 80.degree. C. and/or by using at least one of the base, the reducing metal and the unsaturated compound in an amount not more than 1.
    Type: Grant
    Filed: March 29, 1984
    Date of Patent: November 19, 1985
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Yasuo Yamazaki, Takehiko Suzuki, Isoo Shimizu, Yasuo Matsumura
  • Patent number: 4535179
    Abstract: Bicyclic oxa prostaglandin endoperoxide analogs, and tricyclic oxa prostaglandin analogs are prepared by reacting norbornadiene palladium dichloride with tertiary butyl-6-hydroxyhexanoate in an oxypalladation reaction to provide an oxypalladium intermediate which can subsequently be elaborated into bicyclic and/or tricyclic 7-oxa prostaglandin endoperoxides. If the intermediate is carbonylated in the presence of an organic amine, preferably diisopropylethylamine, the compound is bicyclic; if the amine is eliminated, the compound is tricyclic. The analogs are novel compounds.
    Type: Grant
    Filed: March 3, 1983
    Date of Patent: August 13, 1985
    Assignee: Iowa State University Research Foundation Inc.
    Inventor: Richard C. Larock
  • Patent number: 4515767
    Abstract: Complexes of radionuclides with a compound of the formula ##STR1## wherein substituents A, B, X and Y are each independently selected from radicals including hydrogen, hydroxyalkyl (wherein the alkyl group contains 2-6 carbon atoms) phosphonic, sulfonic, methylenephosphonic, methylene-, ethylene- and propylene-sulfonic, carboxylic acid radicals (having 2-4 carbon atoms) and the alkali or alkaline earth metal, ammonia and amine salts, thereof and wherein at least one A, B, X and Y is methylenephosphonic acid or a salt thereof. Tc-99m complexes have been found useful for imaging the skeletal structure of animals.
    Type: Grant
    Filed: June 20, 1983
    Date of Patent: May 7, 1985
    Assignee: The Dow Chemical Company
    Inventors: Jaime Simon, David A. Wilson, Wynn A. Volkert
  • Patent number: 4514396
    Abstract: 13, 14 didehydro-15 cyclic prostacyclins have been prepared.
    Type: Grant
    Filed: September 28, 1983
    Date of Patent: April 30, 1985
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Nicola Mongelli, Carmelo Gandolfi
  • Patent number: 4508704
    Abstract: New stable complexing agents for Tc-99m which are phosphonate derivatives of bicycloheptane bis(alkylamines) have been found which are useful in imaging the skeletal system in animals. The complexes readily clear through the kidneys with large amounts being taken up in the bone. The ratio of uptake in bone to that in soft tissue is high.
    Type: Grant
    Filed: February 27, 1984
    Date of Patent: April 2, 1985
    Assignee: The Dow Chemical Company
    Inventors: Jaime Simon, David A. Wilson, Wynn A. Volkert
  • Patent number: 4504671
    Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: March 12, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
  • Patent number: 4500470
    Abstract: New compounds have been prepared from dicyclopentadiene bis(methylamine) which have the following formula ##STR1## wherein substituents A, B, X and Y each are independently selected from radicals including hydrogen, hydroxyalkyl (wherein the alkyl group contains 2-6 carbon atoms) phosphonic, sulfonic, hydroxyethyl- and hydroxypropyl-sulfonic, methylenephosphonic methylene-, ethylene- and propylenesulfonic, alkylcarboxylic acid radicals (having 2-4 carbon atoms) and the alkali or alkaline earth metal, ammonia and amine salts of any of the phosphonic, sulfonic or carboxylic acid derivatives. At least one of the substituents must be other than a hydrogen.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: February 19, 1985
    Assignee: The Dow Chemical Company
    Inventor: David A. Wilson
  • Patent number: 4432885
    Abstract: Decalins of the formula ##STR1## wherein ring A is aromatic or a trans-1,4-disubstituted cyclohexane ring; R.sup.2 is methyl, --CH.sub.2 R', --OR', --CO--R', --CN, --COOH, --CO--OR', --CO--SR' or --O--CO--R'; R.sup.1 is hydrogen, methyl, --CH.sub.2 R, --OR or --CH.sub.2 OR, or when R.sup.2 is methyl, --CH.sub.2 R', --OR' or --CO--R', R.sup.1 also can be --CN, --COOH, --CO--OR, --CO--SR or --O--CO--R; R and R' each are alkyl; and R.sup.1 and R.sup.2 each have up to 12 carbon atoms and together have at most 14 carbon atoms,their racemates and optically active antipodes, are described. Liquid crystalline mixtures comprising Compound I as well as their use in electro-optical devices also are disclosed.
    Type: Grant
    Filed: December 9, 1981
    Date of Patent: February 21, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Kuno Schleich
  • Patent number: 4401601
    Abstract: A process for the preparation of tetrasubstituted cyclopropane compounds of the formula ##STR1## wherein Y is selected from the group consisting of --CN and --COOR, R is selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are individually selected from alkyl of 1 to 4 carbon atoms or R.sub.1 and R.sub.2 or R.sub.3 and R.sub.4 together with the carbon atoms to which they are attached form a carbon homocycle of 3 to 6 carbon atoms with the 2 substituents not forming the ring being alkyl of 1 to 4 carbon atoms or R.sub.1 and R.sub.2 on the one hand and R.sub.3 and R.sub.4 on the other together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms which are useful intermediates for the preparation of insecticidal esters and novel intermediates.
    Type: Grant
    Filed: March 23, 1981
    Date of Patent: August 30, 1983
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4400393
    Abstract: A novel bicyclooctane derivative represented by the formula: ##STR1## wherein R.sub.1 is hydrogen or C.sub.1-4 alkyl, X is ethylene or vinylene, and Y.sub.1 and Y.sub.2 are independently hydrogen or a hydroxyl-protecting group, or a pharmaceutically acceptable salt of said compound in which R.sub.1 is hydrogen. Said compound and pharmaceutically acceptable salt are chemically stable, have platelet anti-aggregation activity without undesirable pharmacological actions and exhibit the duration of high biological activity.
    Type: Grant
    Filed: March 24, 1981
    Date of Patent: August 23, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shunsuke Sami, Akihiko Sugie, Keiichi Ono, Hajime Kawakami, Atsuyuki Kojima, Junki Katsube
  • Patent number: 4361577
    Abstract: .omega.-Nor-cycloalkyl-13,14-dehydro-prostaglandin compounds, specifically 5c-9-oxo-11.alpha.,15S-dihydroxy-20,19,18-tirnor-17-cyclohexyl-prost-5-en- 13-ynoic acid, the esters and salts thereof, having antiulcer and luteolytic activity, are disclosed.
    Type: Grant
    Filed: February 2, 1979
    Date of Patent: November 30, 1982
    Assignee: Carlo Erba - S.p.A.
    Inventors: Carmelo Gandolfi, Renato Pellegata, Roberto Ceserani, Maria M. Usardi
  • Patent number: 4349689
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: September 14, 1982
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff