Tricyclo Ring System Patents (Class 562/499)
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Publication number: 20030018065Abstract: This invention provides processes for preparing a group of novel bridged tricyclic compounds having the formula: 1Type: ApplicationFiled: June 27, 2002Publication date: January 23, 2003Applicant: WyethInventors: Alexander Alexei Greenfield, John Anthony Butera
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Patent number: 6492422Abstract: 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: GrantFiled: March 27, 2002Date of Patent: December 10, 2002Assignee: Warner-Lambert CompanyInventors: Patrick Michael O'Brien, Joseph Armand Picard, Drago Robert Sliskovic
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Patent number: 6476258Abstract: 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: GrantFiled: July 5, 2000Date of Patent: November 5, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Masashi Komatsu, Junichi Ishikawa
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Patent number: 6448413Abstract: 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: GrantFiled: November 30, 2001Date of Patent: September 10, 2002Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Csaba Santa, Zoltan Tuba, Sandor Maho, Janos Szeles, Gabor Balogh, Janos Brlik, Ferenc Trischler, Gabriella Szilagyi, Erika Bakcsi
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Publication number: 20020086815Abstract: The present invention provides illudin analogs of the general formula I: 1Type: ApplicationFiled: November 5, 2001Publication date: July 4, 2002Applicant: The Regents of the University of CaliforniaInventors: Trevor C. McMorris, Michael J. Kelner
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Patent number: 6392104Abstract: 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: GrantFiled: November 10, 1998Date of Patent: May 21, 2002Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano, Naruhisa Hirai
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Patent number: 6365768Abstract: 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: GrantFiled: May 12, 2000Date of Patent: April 2, 2002Assignees: Nereus Pharmaceuticals, Inc., University of CaliforniaInventors: Michael Palladino, Emmanuel A. Theodorakis
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Patent number: 6020370Abstract: 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: GrantFiled: May 19, 1998Date of Patent: February 1, 2000Assignee: Warner-Lambert CompanyInventors: David Christopher Horwell, Justin S. Bryans, Clare O. Kneen, Andrew I. Morrell, Giles S. Ratcliffe
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Patent number: 5998471Abstract: Compounds of the formula ##STR1## the symbols have the meaning described in the specification.Type: GrantFiled: August 11, 1998Date of Patent: December 7, 1999Assignee: Allergan Sales, Inc.Inventors: Alan T. Johnson, Min Teng, Vidyasagar Vuligonda, Richard L. Beard, Samuel J. Gillett, Tien T. Duong, Roshantha A. Chandraratna
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Patent number: 5770763Abstract: 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: GrantFiled: August 30, 1996Date of Patent: June 23, 1998Assignee: The Board of Regents of the Univ. of MichiganInventors: David C. Martin, Jeffrey S. Moore, Larry J. Markoski, Kenneth A. Walker, Gary E. Spilman
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Patent number: 5730903Abstract: 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: GrantFiled: December 19, 1995Date of Patent: March 24, 1998Assignee: Fuji Photo Film Co., Ltd.Inventor: Masaki Okazaki
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Patent number: 5723494Abstract: 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: GrantFiled: September 11, 1995Date of Patent: March 3, 1998Assignee: Rotta Research Laboratorium S.P.A.Inventors: Francesco Makovec, Walter Peris, Lucio C. Rovati, Luigi A. Rovati
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Patent number: 5670696Abstract: 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: GrantFiled: September 1, 1995Date of Patent: September 23, 1997Assignee: Arakawa Chemical Industires Ltd.Inventors: Takaharu Tsuno, Hideki Kobayashi
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Patent number: 5595996Abstract: 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: GrantFiled: October 25, 1994Date of Patent: January 21, 1997Assignee: Merck & Co., Inc.Inventors: Donald W. Graham, Josephine R. Carlin, Shuet-Hing L. Chiu, Richard L. Tolman
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Patent number: 5578726Abstract: 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: GrantFiled: November 10, 1994Date of Patent: November 26, 1996Assignee: Merck & Co., Inc.Inventors: Raman K. Bakshi, Gary H. Rasmusson
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Patent number: 5576355Abstract: 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: GrantFiled: December 15, 1993Date of Patent: November 19, 1996Assignee: Mobil Oil Corp.Inventors: Catherine S. H. Chen, Dong-ming Shen
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Patent number: 5545654Abstract: 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: GrantFiled: January 3, 1994Date of Patent: August 13, 1996Assignee: Biochemie Gesellschaft m.b.H.Inventor: Ingolf Macher
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Patent number: 5434274Abstract: Neuroactive benz[e]indene compounds ##STR1## are prepared by a total synthesis from the following three starting materials ##STR2##Type: GrantFiled: March 2, 1994Date of Patent: July 18, 1995Assignee: Washington UniversityInventors: Douglas F. Covey, Yuefei Hu, Mingcheng Han, Charles F. Zorumski
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Patent number: 5405870Abstract: 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: GrantFiled: November 4, 1993Date of Patent: April 11, 1995Assignee: Sankyo Company, LimitedInventors: Kazuo Koyama, Shigeo Amemiya, Koichi Kojima, Shinsaku Kobayashi
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Patent number: 5405978Abstract: 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: GrantFiled: November 24, 1993Date of Patent: April 11, 1995Assignee: The Upjohn CompanyInventor: Paul M. Herrinton
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Patent number: 5292906Abstract: 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: GrantFiled: January 14, 1993Date of Patent: March 8, 1994Assignee: Washington UniversityInventors: Douglas F. Covey, Yuefei Hu, Charles F. Zorumski
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Patent number: 5228898Abstract: 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: GrantFiled: February 3, 1992Date of Patent: July 20, 1993Assignee: Nippon Soda Co., Ltd.Inventors: Akiyoshi Ueda, Shigemi Suga, Hiroyuki Adachi, Toshio Aihara, Kazuyuki Tomida, Hideki Yamagishi, Hideo Hosaka
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Patent number: 5206415Abstract: 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: GrantFiled: December 20, 1991Date of Patent: April 27, 1993Assignee: Washington UniversityInventors: Douglas F. Covey, Yuefei Hu, Charles F. Zorumski
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Patent number: 5191115Abstract: 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: GrantFiled: February 5, 1991Date of Patent: March 2, 1993Assignee: AtochemInventors: Veronique Lazzeri, Roger Gallo, Rachid Jalal
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Patent number: 4976893Abstract: 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: GrantFiled: June 18, 1986Date of Patent: December 11, 1990Assignee: Hoechst AktiengesellschaftInventor: Ernst I. Leupold
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Patent number: 4973740Abstract: 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: GrantFiled: September 28, 1989Date of Patent: November 27, 1990Assignees: Mitsubishi Gas Chemical Co., Inc., Kao CorporationInventors: Masami Ishihara, Takeshi Morokuma
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Patent number: 4927963Abstract: 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: GrantFiled: April 28, 1989Date of Patent: May 22, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Keith A. M. Walker, Denis J. Kertesz
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Patent number: 4921526Abstract: 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: GrantFiled: November 27, 1987Date of Patent: May 1, 1990Assignee: Sandoz Ltd.Inventors: Shy-Fuh Lee, Gary W. Luehr, Carol R. Scott, Werner Trueb
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Patent number: 4906769Abstract: 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: GrantFiled: April 6, 1989Date of Patent: March 6, 1990Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Franz Merger, Hans-Juergen Gosch
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Patent number: 4777184Abstract: 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: GrantFiled: April 29, 1986Date of Patent: October 11, 1988Assignee: Sankyo Company LimitedInventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Nobuyoshi Iwata, Takeshi Oshima
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Patent number: 4760175Abstract: 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: GrantFiled: May 6, 1985Date of Patent: July 26, 1988Assignee: General Foods CorporationInventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
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Patent number: 4683330Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: July 28, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4680307Abstract: 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: GrantFiled: January 26, 1984Date of Patent: July 14, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Masami Muraoka, Toshio Nakamura, Akihiko Sugie, Keiichi Ono, Michihiro Yamamoto
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Patent number: 4668814Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: May 26, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4656307Abstract: 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: GrantFiled: July 15, 1985Date of Patent: April 7, 1987Assignee: Nippon Oil Co., Ltd.Inventors: Yoshihiro Kobori, Tetsuya Takezono
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Patent number: 4602107Abstract: 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: GrantFiled: July 18, 1983Date of Patent: July 22, 1986Assignee: Kao CorporationInventors: Yoshiaki Fujikura, Naotake Takaishi, Yoshiaki Inamoto
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Patent number: 4585893Abstract: 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: GrantFiled: July 18, 1983Date of Patent: April 29, 1986Assignee: KAO CorporationInventors: Yoshiaki Fujikura, Naotake Takaishi, Yoshiaki Inamoto
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Patent number: 4582698Abstract: 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: GrantFiled: September 19, 1983Date of Patent: April 15, 1986Assignee: The Dow Chemical CompanyInventors: Jaime Simon, David A. Wilson, Wynn A. Volkert
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Patent number: 4554360Abstract: 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: GrantFiled: March 29, 1984Date of Patent: November 19, 1985Assignee: Nippon Petrochemicals Company, LimitedInventors: Yasuo Yamazaki, Takehiko Suzuki, Isoo Shimizu, Yasuo Matsumura
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Patent number: 4535179Abstract: 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: GrantFiled: March 3, 1983Date of Patent: August 13, 1985Assignee: Iowa State University Research Foundation Inc.Inventor: Richard C. Larock
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Patent number: 4515767Abstract: 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: GrantFiled: June 20, 1983Date of Patent: May 7, 1985Assignee: The Dow Chemical CompanyInventors: Jaime Simon, David A. Wilson, Wynn A. Volkert
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Patent number: 4514396Abstract: 13, 14 didehydro-15 cyclic prostacyclins have been prepared.Type: GrantFiled: September 28, 1983Date of Patent: April 30, 1985Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Nicola Mongelli, Carmelo Gandolfi
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Patent number: 4508704Abstract: 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: GrantFiled: February 27, 1984Date of Patent: April 2, 1985Assignee: The Dow Chemical CompanyInventors: Jaime Simon, David A. Wilson, Wynn A. Volkert
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Patent number: 4504671Abstract: 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: GrantFiled: October 15, 1982Date of Patent: March 12, 1985Assignee: PPG Industries, Inc.Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
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Patent number: 4500470Abstract: 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: GrantFiled: April 18, 1983Date of Patent: February 19, 1985Assignee: The Dow Chemical CompanyInventor: David A. Wilson
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Patent number: 4432885Abstract: 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: GrantFiled: December 9, 1981Date of Patent: February 21, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Kuno Schleich
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Patent number: 4401601Abstract: 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: GrantFiled: March 23, 1981Date of Patent: August 30, 1983Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4400393Abstract: 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: GrantFiled: March 24, 1981Date of Patent: August 23, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Shunsuke Sami, Akihiko Sugie, Keiichi Ono, Hajime Kawakami, Atsuyuki Kojima, Junki Katsube
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Patent number: 4361577Abstract: .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: GrantFiled: February 2, 1979Date of Patent: November 30, 1982Assignee: Carlo Erba - S.p.A.Inventors: Carmelo Gandolfi, Renato Pellegata, Roberto Ceserani, Maria M. Usardi
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Patent number: 4349689Abstract: 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: GrantFiled: December 22, 1980Date of Patent: September 14, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff