Tricyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/458)
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Patent number: 6395773Abstract: In order to provide antibacterial agents for drug-resistant bacteria and anti-Chlamydia agents, the furanonaphthoquinone derivative represented by the following formula (1): wherein each R may be the same or different, representing any one of the following (a) to (e): (wherein R′ is a hydrogen atom, alkyl group, hydroxyalkyl group, or alkoxyalkyl group), or two mutually adjacent Rs may be bonded via an oxygen atom to form a heterocyclic ring is used as the effective component.Type: GrantFiled: July 23, 2001Date of Patent: May 28, 2002Assignee: Japan Science and Technology CorporationInventors: Keiichi Hirai, Kumiko Nagata, Junko Koyama, Toshio Kishimoto
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Patent number: 6392059Abstract: Intermediates for the preparation of himbacine exhibiting muscarinic M2 receptor antagonism, which are hydronaphtho[2,3-c]furan derivatives represented by general formula (1) or intermediates for the preparation thereof: wherein R1 is lower alkyl or aralky; R2 is hydrogen, lower alkyl or aralkyl; R3 and R4 together represent oxygen or methylene, or alternatively R4 is hydroxyl, lower alkoxy, aralkyloxy or lower acyloxy, with R3 being hydrogen; R5 and R6 together represent oxygen, or alternatively R6 is hydroxyl, lower alkxy, aralkyloxy or lower acyloxy, with R5 being hydrogen; and either of the broken lines is a single bond and the other thereof is a double bond, or alternatively both are single bonds.Type: GrantFiled: June 7, 2001Date of Patent: May 21, 2002Assignees: Sagami Chemical Reasearch Center, Kyorin Pharmaceutical Co., Ltd.Inventors: Shiro Terashima, Masanori Takadoi, Akihiro Ishiwata, Tadashi Katoh
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Patent number: 6380404Abstract: Norlabdane oxide, which is a well known fragrance material having ambergris-type odors, is prepared from 12-acetoxy-norlabdane oxide by a hydrogenation reaction.Type: GrantFiled: May 29, 2001Date of Patent: April 30, 2002Assignee: Quest International B.V.Inventors: Paul Nicholas Davey, Chi-Lam Tse
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Publication number: 20020019380Abstract: A compound selected from those of formula (I): 1Type: ApplicationFiled: April 12, 2001Publication date: February 14, 2002Inventors: Jean-Louis Peglion, Aimee Dessinges, Bertrand Goument, Mark Millan, Francoise Lejeune, Mauricette Brocco
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Patent number: 6340693Abstract: The present invention provides a protective agent for nervous system structural cells comprising a prostaglandin I derivative, preferably a prostaglandin I2 derivative, particularly beraplost, as an active component. This medicine exhibits excellent effects as a protective agent for nervous system structural cells, and is effective as an excellent agent for preventing or curing cerebrovascular disorder, cerebral nerve cell disorder, ischemic cerebral disorder, dementia, and peripheral nerve disorder due to diabetic or the like.Type: GrantFiled: February 16, 1999Date of Patent: January 22, 2002Assignee: Toray Industries, Inc.Inventors: Hajimu Kurumatani, Susumu Matsuda, Mie Kainoh
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Publication number: 20020006944Abstract: A compound of the formula: 1Type: ApplicationFiled: March 7, 2001Publication date: January 17, 2002Inventors: Shigenori Ohkawa, Masaki Setoh, Zen-ichi Terashita
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Patent number: 6323348Abstract: The present invention provides a process for producing an optically active compound of cycloalkyl[b]benzofuran using a readily available optically active compound as a starting material by a reaction using a transition metal or the Mitsunobu reaction, or a combination thereof, followed by a cyclization reaction using a metal or an organometallic reagent. The process can exclude the needs of complicated optical resolution steps as well as enzyme reactions that requires a large amount of solvent and long reaction time besides repeatability is hardly obtained, providing a very useful production process that can apply for not only laboratory preparation but also for industrial scale productions.Type: GrantFiled: February 14, 2000Date of Patent: November 27, 2001Assignee: Toray Industries, Inc.Inventors: Hisao Nishiyama, Hisanori Wakita, Hiroshi Nagase
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Patent number: 6300339Abstract: The present invention relates to compounds of formula (I) wherein A, B, Q, T, X, Y, Z, R5, R6, R7, R8, Ar, k, m, n and p are as defined in the specification. These compounds are useful in treating or preventing conditions mediated by nuclear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR).Type: GrantFiled: October 19, 1999Date of Patent: October 9, 2001Assignees: Novo Nordisk A/S, Dr. Reddy's Research FoundationInventors: Lone Jeppesen, Paul Stanley Bury, Per Sauerberg
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Patent number: 6262271Abstract: A series of bioactive analogs of (+)-CC-1065 (1) and the duocarmycins 2 and 3 are synthesized. The bioactive analogs include either iso-CI or iso-CBI (6 and 7) as a DNA alkylation subunit. Conjugated to the DNA alkylating subunits are a variety of DNA binding subunits. The bioactive analogs maintain their DNA selectivity and display enhanced reactivity.Type: GrantFiled: April 12, 2000Date of Patent: July 17, 2001Assignee: The Scripps Research InstituteInventor: Dale L. Boger
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Patent number: 6251936Abstract: This invention provides compounds of Formula I having the structure E is S, SO, SO2, O, or NR1c; X is hydrogen, halogen, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, CN, aryl, aralkyl of 6-12 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, hydroxyaralkyl of 6-12 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, aryloxy; arylalkoxy, nitro, amino, NR2R2a, NR2COR2a, cycloalkylamino of 3-8 carbon atoms, morpholino, alkylsulfanyl of 1-6 carbon atoms, arylsulfanyl, pyridylsulfanyl, 2-N,N-dimethylaminoethylsulfanyl, —OCH2CO2R2b or —COR2c; Z1 and Z2 are each, independently, hydrogen, halogen, CN, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, cycloalkyl of 3-8 carbon atoms, nitro, amino, —NR1R1a, —NR1COR1a, cycloalkylamino of 3-8 carbon atoms, morpholino, or OR8, or Z1 and Z2 may be taken together as a diene unit having the formula —CH═CR9—CR10═CR11—; or a pharmaceutically acceptable salt thType: GrantFiled: May 10, 1999Date of Patent: June 26, 2001Assignee: American Home Products CorporationInventors: Jay E. Wrobel, Arlene J. Dietrich, Madelene M. Antane
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Patent number: 6218429Abstract: A compound of the formula: wherein R1 is an optionally substituted hydrocarbon, amino or heterocyclic group; R2 is H or an optionally substituted hydrocarbon group; R3 is H or an optionally substituted hydrocarbon or heterocyclic group; X is CHR4, NR4, O or S in which R4 is H or an optionally substituted hydrocarbon group; Y is C, CH or N; ring A is optionally substituted 5- to 7-membered ring; ring B is an optionally substituted benzene ring; and m is 1 to 4, or a salt thereof, a process for producing it, an intermediate for the production and a pharmaceutical composition comprising it are provided.Type: GrantFiled: May 10, 1999Date of Patent: April 17, 2001Assignee: Takeda Chemical Industries, Ltd.Inventors: Shigenori Ohkawa, Osamu Uchikawa, Kohji Fukatsu, Masaomi Miyamoto
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Patent number: 6121271Abstract: This invention provides compounds of Formula I having the structure whereinR.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, W, R.sup.9, X, R.sup.6, p, Y, Z, R.sup.7, and R.sub.8 are as defined in the specification, or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.Type: GrantFiled: May 10, 1999Date of Patent: September 19, 2000Assignee: American Home Products CorporationInventors: Paul J. Dollings, Arlene J. Dietrich, Jay E. Wrobel
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Patent number: 6107335Abstract: The compounds 18.beta., 19.beta.-diacetyloxy-18.alpha., 19.alpha.-epoxy-3, 13(16), 14-clerodatrien-2-one (Esculentin A) and 18.beta., 19.beta.-diacetyloxy-18.alpha., 19.alpha.-epoxy-3, 12, 14-clerodatrien-2.beta.-isovaleryloxy-6.beta., 7.alpha.-diol (Esculentin B) obtained from plants belonging to the Samydaceae family, particularly Casearia esculenta, a process for their preparation, and their use in the manufacture of medicaments. The compounds are particularly useful as anti-inflammatory and/or anti-cancer agents.Type: GrantFiled: November 17, 1998Date of Patent: August 22, 2000Assignee: Hoechst Marion Roussel Deutschland GmbHInventors: Swati Bal-Tembe, Erra Koteswara Satya Vijaya Kumar, Vijay Bhagwan Deore, Kalpana Sanjay Joshi
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Patent number: 6103914Abstract: Optically active materials of tricyclic compounds, for example, cyclopenta [b] benzofuran derivatives represented by the following formula: ##STR1## wherein R.sub.1, R.sub.2, Y and Z independently represent hydrogen, halogen, an alkyl group, or an aryl group; and n represents 0 to 4, are directly produced by adding an optically active alcohol, amine and/or metal salt thereof.Type: GrantFiled: October 20, 1998Date of Patent: August 15, 2000Assignee: Toray Industries, Inc.Inventors: Hisao Nishiyama, Hiroshi Nagase, Hisanori Wakita
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Patent number: 6046233Abstract: The present invention relates to an agent for treating cor pulmonale containing as an active ingredient a prostaglandin I.sub.2 derivative represented by the following formula, or a pharmacologically acceptable salt thereof. The agent exhibits excellent effects in oral or parenteral administration.Type: GrantFiled: January 3, 1997Date of Patent: April 4, 2000Assignee: Toray Industries, Inc.Inventors: Reiji Kasukawa, Masayuki Miyata, Yuji Ueno, Hiroshi Koike, Hajimu Kurumatani, Shintaro Nishio
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Patent number: 6034239Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is an optionally substituted hydrocarbon, amino or heterocyclic group; R.sup.2 is H or an optionally substituted hydrocarbon group; R.sup.3 is H or an optionally substituted hydrocarbon or heterocyclic group; X is CHR.sup.4, NR.sup.4, O or S in which R.sup.4 is H or an optionally substituted hydrocarbon group; Y is C, CH or N; ring A is optionally substituted 5- to 7-membered ring; ring B is an optionally substituted benzene ring; and m is 1 to 4, or a salt thereof, a process for producing it, an intermediate for the production and a pharmaceutical composition comprising it are provided.Type: GrantFiled: March 6, 1997Date of Patent: March 7, 2000Assignee: Takeda Chemical Industries, Ltd.Inventors: Shigenori Ohkawa, Osamu Uchikawa, Kohji Fukatsu, Masaomi Miyamoto
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Patent number: 5849781Abstract: The invention relates to a compound selected from these of formula (I): ##STR1## in which R.sub.7, R.sub.8, Y, n and A are as defined in the description, and medicinal product containing the same useful for treating a disorder of the melatoninergic system.Type: GrantFiled: October 1, 1997Date of Patent: December 15, 1998Assignee: Adir Et CompagnieInventors: Michel Langlois, Monique Mathe-Allainmat, Philippe Delagrange, Pierre Renard, Beatrice Guardiola
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Patent number: 5843988Abstract: The present invention provides novel cyclopropachromen-carboxylic acid derivatives having an antagonistic activity against metabotropic glutamate receptors and its pharmaceutically acceptable salts. Cyclopropachromen-carboxylic acid derivatives and its pharmaceutically acceptable salts represented by the following general formula (1): ##STR1## ?wherein A denotes an oxygen atom, hydroxyimino group, an alkyloxyimino group having 1 to 5 carbon atoms, or the group .dbd.N--O--(CH.sub.2).sub.n -NR.sup.1 R.sup.2 (where n represents an integer of 2 to 8, and each of R.sup.1 and R.sup.2 independently represents a hydrogen atom or alkyl group having 1 to 5 carbon atoms, respectively); B denotes the group --COOR.sup.3 (where R.sup.3 represents a hydrogen atom or alkyl group having 1 to 5 carbon atoms) or the group --CONR.sup.4 R.sup.5 (where R.sup.4 and R.sup.5 independently represent a hydrogen atom, alkyl group having 1 to 5 carbon atoms, alkenyl group having 2 to 5 carbon atoms and an aminoalkyl group.Type: GrantFiled: April 18, 1997Date of Patent: December 1, 1998Assignee: Suntory LimitedInventors: Hirokazu Annoura, Atsuko Fukunaga, Toshio Tatasuoka, Yoshiko Horikawa
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Patent number: 5843986Abstract: A compound selected from those of formula (I): ##STR1## in which A, Y, R.sup.1, R.sup.2 and R.sup.3 are as defined in the description, and a medicinal product containing the same useful for treating a mammal afflicted with a disorder of the melatoninergic system.Type: GrantFiled: October 19, 1995Date of Patent: December 1, 1998Assignee: Adir et CompagnieInventors: Daniel Lesieur, Patrick Depreux, Veronique Leclerc, Hamid Ait Mansour, Philippe Delagrance, Pierre Renard
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Patent number: 5840927Abstract: Novel anti-microbial sesquiterpene compounds isolated from the fruit bodies of Roseofomes subflexibilis (Hounen-take) having the general formula ##STR1##Type: GrantFiled: September 26, 1997Date of Patent: November 24, 1998Assignee: Toa Gosei Co., Ltd.Inventors: Shigeo Nozoe, Akira Takahashi, Jun-ich Masuda, Ken-ichi Tanaka, Hideo Suzuki
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Patent number: 5824700Abstract: The invention relates to .beta.-lapachone derivatives of formula II and compositions containing said compounds: ##STR1## wherein, R.sup.5, R.sup.6 and R.sup.7 are as defined in the specification. The compounds are potent inhibitors of neoplastic cell growth and proliferation.Type: GrantFiled: February 20, 1996Date of Patent: October 20, 1998Assignee: Wisconsin Alumni Research FoundationInventors: Benjamin J. Frydman, Donald T. Witiak, Jerry Shunneng Sun, Andrew H. Geiser
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Patent number: 5821375Abstract: The invention concerns a process for preparing (-)-norlabdane oxide from sclareol oxide comprising the steps of:I converting sclareol oxide to 12-acetylnorlabdane oxide by oxidation with an organic hydroperoxide;II converting 12-acetylnorlabdane oxide to 12-acetoxy-norlabdane oxide by oxidation with an organic peracid.Step I is preferably performed with tert-butyl hydroperoxide and step II with peracetic acid.Sclareol oxide may be prepared from sclareol by ozonolysis followed by treatment with alkaline hydrogen peroxide. 12-Acetoxy-norlabdane oxide is preferably converted to norlabdane oxide by reduction with NaBH.sub.4 in the presence of a transition metal salt.Type: GrantFiled: August 1, 1997Date of Patent: October 13, 1998Assignee: Quest International B.V.Inventors: Paul Nicholas Davey, Laurence Sidney Payne, Chi-lam Tse
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Patent number: 5811560Abstract: The invention pertains to a method for preparing 8-alpha,12-oxido-13,14,15,16, -tetranorlabdane by cyclizing a mixture of hydroxy-olefins (I)-(III. See the specification for their formulae. The cyclization is carried out in the presence of 10 to 100 wt. % acid, relative to the mixture of compounds (I) to (III).Type: GrantFiled: May 5, 1997Date of Patent: September 22, 1998Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Georg Knuebel, Andreas Bomhard, Thomas Markert
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Patent number: 5726325Abstract: The present invention relates to tricyclic compounds represented by general formula (I) which are useful as therapeutic agents for urinary incontinence: ##STR1## wherein R.sup.1 represents hydrogen and the like; --X.sup.1 --X.sup.2 --X.sup.3 -- represents --CR.sup.2 .dbd.CR.sup.3 --CR.sup.4 .dbd.CR.sup.5 -- (wherein R.sup.2, R.sup.3, R.sup.4, and R.sup.5 represent hydrogen and the like) and the like; and Y represents --CH.sub.2 O-- and the like.Type: GrantFiled: June 6, 1997Date of Patent: March 10, 1998Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Makoto Yoshida, Shin-ichi Sasaki, Shigeru Aono, Shigeki Fujiwara, Haruki Takai, Tsuyoshi Yamagata, Ken Nagashima, Akira Karasawa
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Patent number: 5716986Abstract: This invention relates to new oxaindene derivatives, a process for the preparation thereof and pharmaceutical compositions comprising the same.The compounds according to the invention are characterized by the general formula (1) ##STR1## wherein R.sup.1 represents lower C.sub.1-4 alkyl, lower C.sub.1-4 alkoxy or lower C.sub.3-6 cycloalkyl,R.sup.2 stands for hydrogen, lower C.sub.1-4 alkyl or lower C.sub.3-6 cycloalkyl,R.sup.3 stands for hydrogen, lower C.sub.1-4 alkyl, lower C.sub.1-4 alkoxy or benzyloxy,X denotes hydrogen, an aliphatic C.sub.1-4 -acyl or benzoyl or naphthoyl group, optionally substituted by 1 or more nitro or C.sub.1-4 -alkoxy group(s) or a group of the formula R.sup.5 R.sup.6 N--R.sup.7 --, wherein R.sup.7 represents lower C.sub.1-4 alkylene and R.sup.5 and R.sup.6 each represent lower C.sub.1-4 alkyl, or R.sup.5 and R.sup.Type: GrantFiled: June 27, 1996Date of Patent: February 10, 1998Assignee: Egis Gyogyszergyar Rt.Inventors: Csaba Szantay, Lajos Novak, Peter Kovacs, Klara Gado, Gabor Gigler, Julianna Takacs nee Bitai, Andras Egyed, Daniel Bozsing, Gyorgy Pirok, Katalin Szemeredi, Margit Csorgo, Sandor Drabant, Gabor Blasko, Gyula Simig, Gabor Kovacs
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Patent number: 5688976Abstract: The invention relates to a process for producing 8.alpha.,12-oxido-13,14,15,16-tetranorlabdane through the cyclizing dehydration of 8.alpha.,12 -dihydroxy-13,14,15,16-tetranorlabdane in the presence of aluminophyllosilicates.Type: GrantFiled: July 3, 1996Date of Patent: November 18, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Georg Knuebel, Andreas Bomhard, Ulf-Armin Schaper, Theo Stalberg, Thomas Markert
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Patent number: 5686586Abstract: A polycyclic aromatic compound having the formula ##STR1## and its salts have useful therapeutic and cosmetic action particularly in psoriasis.In the formula, X represents --CH.dbd.CH--, O or S,R.sub.1 represents hydrogen, branched alkyl having 3-15 carbon atoms, alkoxy having 1-6 carbon atoms or 1-adamantyl, R.sub.2 represents hydroxy, hydrogen, linear or branched alkyl having 1-15 carbon atoms or alkoxy having 1-6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, or R.sub.1 and R.sub.2 together with the adjacent carbon atoms of the naphthalene ring form a 5 or 6 chain ring optionally substituted by at least one lower alkyl radical, or interrupted by an oxygen atom,R.sub.3 represents --CH.sub.2 OH or --COR.sub.4, or --CH.sub.3 when R.sub.1 and R.sub.2 taken together form a 5 or 6 chain ring,R.sub.4 represents --OR.sub.5 or ##STR2## R.sub.Type: GrantFiled: October 4, 1996Date of Patent: November 11, 1997Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Braham Shroot, Jacques Eustache, Oliver Watts, Jean-Michel Bernardon, Philippe Nedoncelle
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Patent number: 5670670Abstract: In a process for the production of 8.alpha.,12-oxido-13,14,15,16-tetranorlabdane by dehydration of 8.alpha.,12-dihydroxy-13,14,15,16-tetranorlabdane (diol), wherein the diol is subjected to cyclizing dehydration in the presence of 5 to 80% by weight, based on the diol, of at least one alumino layer silicate selected from K catalysts which have an acid charge of less than 100 mval/100 g.Type: GrantFiled: May 31, 1996Date of Patent: September 23, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Georg Knuebel, Andreas Bomhard, Ulf-Armin Schaper, Theo Stalberg, Thomas Markert
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Patent number: 5665765Abstract: New compounds of formula: ##STR1## wherein: A-B, n and Y are as defined in the description,their optical isomers and physiologically tolerable salts thereof with appropriate acids.The products of the invention may be used as medicaments.Type: GrantFiled: September 27, 1996Date of Patent: September 9, 1997Assignee: Adir et CompagnieInventors: Jean-Louis Peglion, Joel Vian, Aimee Dessinges, Mark Millan, Valerie Audinot
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Patent number: 5639894Abstract: A process for the carbonylation of allylic alcohols such as nerolidol, farnesol, or their monocyclic analogues with carbon monoxide at a pressure of at least 30 bar in the presence of a polar solvent and a palladium halide catalyst, optionally an alkali metal halide salt, and optionally an alcoholic solvent. The carbonylated product may then be reduced to the corresponding alcohol, which is cyclized in the presence of Lewis or Bronsted acids to afford an ambergris fragrance compound.Type: GrantFiled: March 23, 1994Date of Patent: June 17, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Jonathan M. Cassel, Steven M. Hoagland, James M. Renga
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Patent number: 5616737Abstract: A process for the stereoselective preparation of (-)3a,6,6,9a-tetramethylperhydronaphtho[2,1-b]furan of the formula Ia ##STR1## by dehydration and cyclization of decahydro-2-hydroxy- 2,5,5,8-tetramethyl-1-naphthaleneethanol using solid acidic catalysts, wherein the decahydro-2-hydroxy- 2,5,5,8-tetramethyl-1-naphthaleneethanol is heated in the molten state at from 80.degree. to 200.degree. C. in the presence of from 10 to 100% by weight, based on the diol, of an active acidic aluminum oxide commercially supplied for (preparative) column chromatography.Type: GrantFiled: July 3, 1996Date of Patent: April 1, 1997Assignee: BASF AktiengesellschaftInventors: Johannes Grimmer, Christoph Martin
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Patent number: 5587486Abstract: 1-amino-2-cyclohexene compounds represented by the following formula (I): ##STR1## wherein the substituents are as defined in the specification, a process for preparing the compounds and their use as intermediates in the production of medicinal and agricultural agents is disclosed.Type: GrantFiled: June 30, 1995Date of Patent: December 24, 1996Assignee: Kuraray Co., Ltd.Inventors: Naoshi Nakagawa, Tadashi Hatanaka, Tatsuhiko Hayashibara, Manzo Shiono
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Patent number: 5508303Abstract: A composition for stimulating hair growth is described. The composition comprises as an effective ingredient a 5,6,7-trinor-4,8-inter-m-phenylene prostaglandin I.sub.2 derivative of the formula (I) or a pharmaceutically acceptable salt thereof.Type: GrantFiled: May 28, 1993Date of Patent: April 16, 1996Assignee: Toray Industries, Inc.Inventors: Masafumi Isogaya, Shintaro Nishio
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Patent number: 5496849Abstract: The present invention discloses sulfonamide derivative represented by the following general formula: ##STR1## [wherein, R.sub.1 is(i) --COOR.sub.2 (where, R.sub.2 is (1) hydrogen, (2) a pharmacologically acceptable cation, or (3) an alkyl having 1 to 14 carbon atoms) or,(ii) --C(.dbd.O)--R.sub.3 (wherein, R.sub.3 represents an alkyl having 1 to 4 carbon atoms); A is(i) --(CH.sub.2)n-- (wherein, n represents an integer of 0 to 3),(ii) --CH.dbd.CH--, or the group:(iii) --O--C(R.sub.4) (R.sub.5)-- (wherein, R.sub.4 and R.sub.5 represent (1) hydrogen or (2) an alkyl having 1 to 4 carbon atoms, and R.sub.4 and R.sub.5 may be identical or different); and,w is NH or --O--], as well as a thromboxane A2 receptor antagonistic drug having said derivative for its active ingredient.Since the compound of the present invention has excellent thromboxane A2 receptor antagonistic action, it can be used as a thromboxane A2 receptor antagonist of high activity and long duration.Type: GrantFiled: May 17, 1994Date of Patent: March 5, 1996Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Atsushi Ohtake, Shintaro Nishio, Kazuhiro Hoshi, Shunji Tsukamoto
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Patent number: 5473085Abstract: Preparation of a methyl ketone intermediate useful in the synthesis of (-)-dodecahydro-3a,6,6, 9a-tetramethyl-naphtho(2,1-b) furan by subjecting (-)-sclareol to ozonolysis in the presence of iodine or iodine-containing compound. The intermediate can be converted to (-)-dodecahydro-3a,6,6,9a-tetramethyl-naphtho(2,1-b) furan by Baeyer-Villiger oxidation followed by reduction of the resulting product in the presence of a Lewis acid.Type: GrantFiled: September 28, 1994Date of Patent: December 5, 1995Assignee: Quest International B.V.Inventors: Derek H. R. Barton, Dennis K. Taylor, Chi-Lam Tse
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Patent number: 5470989Abstract: Stereoisomer mixtures of 8,12-oxido-13,14,15,16-tetranorlabdane are obtained in yields of at least 95% by dehydrating cyclization of stereoisomer mixtures of 8,12-dihydroxy-13,14,15,16-tetranorlabdane in the presence of acid-loaded aluminum oxide.Type: GrantFiled: January 18, 1994Date of Patent: November 28, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Thomas Gerke
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Patent number: 5463089Abstract: Synthesis of (-)-dodecahydro-3a,6,6,9a-tetramethyl-naphtho(2,1-b)furan from sclareol in a three-stage process.Type: GrantFiled: July 22, 1994Date of Patent: October 31, 1995Assignee: Quest International B.V.Inventors: Derek H. R. Barton, Shyamal I. Parekh, Dennis K. Taylor, Chi-lam Tse
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Patent number: 5441930Abstract: The isomeric 11-oxa-tricyclo[7.3.0.0.sup.2,6 ]dodecene derivatives proposed are valuable new odoriferous substances characterized by their different nuances of intense woody notes and extremely high persistence. They can be mixed with each other, or with other odoriferous substances, in widely varying proportions to give new perfume compositions, generally containing between 1 and 50% by wt., relative to tile weight of the whole composition, of the derivatives proposed.Type: GrantFiled: July 8, 1994Date of Patent: August 15, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Klaus Bruns, Michael Dischmann, Werner Faber, Michael Meiertoberens
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Patent number: 5420310Abstract: The present invention provides a process for preparing 5,6,7-trinor-4,8-inter-m-phenylene PGI.sub.2 derivative using 3a,8b-cis-dihydro-3H-5,7-dibromocyclopenta[b]benzofuran as a starting material, as well as compounds which are intermediates.Type: GrantFiled: November 20, 1992Date of Patent: May 30, 1995Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Hiroshi Nagase, Yutaka Hosono, Hisanori Wakita, Koji Kawai, Hideo Yoshiwara
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Patent number: 5416069Abstract: Novel naphthofuran derivatives of the formula ##STR1## wherein R represents hydrogen, methyl or ethyl. The compounds of formula I are valuable (amber) odorants and also flavorants. Odorant and flavorant compositions employing (I) as well as processes for making them are also described.Type: GrantFiled: July 14, 1994Date of Patent: May 16, 1995Assignee: Givaudan-Roure CorporationInventor: Peter Naegeli
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Patent number: 5401768Abstract: Disclosed are 2,5,6,7-tetranor-4,8-inter-m-phemylene PGI.sub.2 derivatives such as 16-methyl-2,5,6,7-tetranor-4,8-inter-m-phenylene PGI.sub.2 and methyl ester thereof, 17-methyl-2,5,6,7-tetranor-4,8-inter-m-phenylene PGI.sub.2 and methyl ester thereof, 15-phenyl-2,5,6,7,16,17,18,19,20-nonanor-4,8-inter-m-phenylene PGI.sub.2, 16-methyl-17-phenyl-2,5,6,7,18,19,20-heptanor-4,8-inter-m-phenylene PGI.sub.2, 16,16-dimethyl-17-phenyl-2,5,6,7,18,19,20-heptanor-4,8-inter-m-phenylene PGI.sub.2, 16-methyl-16-phenoxy-2,5,6,7,17,18,19,20-octanor-4,8-inter-m-phenylene PGI.sub.2, 16-methyl-16-phenoxy-2,5,6,7,18,19,20-heptanor-4,8-inter-m-phenylene PGI.sub.2 and methyl ester thereof, and 3-decarboxy-3-hydroxymethyl-16-methyl-16-phenoxy-2,5,6,7,18,19,20-heptanor -4,8-inter-m-phenylene PGI.sub.2, which are useful as pharmaceuticals.These compounds are useful as an antiulcer drug, antihypertensive drug, antithrombus drug or the like.Type: GrantFiled: July 13, 1993Date of Patent: March 28, 1995Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Toshiya Takahashi, Atsushi Ohtake, Hisanori Wakita, Shintaro Nishio
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Patent number: 5399587Abstract: The present invention relates to novel potassium channel agonists which are useful in activating the calcium activated Maxi-K potassium channel in mammalian neuronal and smooth muscle tissue. The claimed compounds are of the general formula: ##STR1## In addition, a novel microbiological process for producing the claimed compounds is described.Type: GrantFiled: December 13, 1993Date of Patent: March 21, 1995Assignee: Merck & Co., Inc.Inventors: Maria L. Garcia, Robert A. Giacobbe, Otto D. Hensens, Gregory J. Kaczorowski, Seok H. Lee, Owen B. McManus, Deborah L. Zink
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Patent number: 5326888Abstract: A process for the carbonylation of allylic alcohols such as nerolidol, farnesol, or their monocyclic analogues with carbon monoxide at a pressure of at least 30 bar in the presence of a polar solvent and a palladium halide catalyst, optionally an alkali metal halide salt, and optionally an alcoholic solvent. The carbonylated product may then be reduced to the corresponding alcohol, which is cyclized in the presence of Lewis or Bronsted acids to afford an ambergris fragrance compound.Type: GrantFiled: October 9, 1990Date of Patent: July 5, 1994Assignee: Henkel Research CorporationInventors: Jonathan M. Cassel, Steven M. Hoagland, James M. Renga
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Patent number: 5304702Abstract: Polyhalogenated organic compounds, such as polychlorinated dibenzodioxines, dibenzofurans, biphenyls, biphenyl ethers, phenols, benzenes and cyclohexanes as well as chlorofluorohydrocarbons are destroyed by reaction with a surplus of strongly basic hydrocarbon-soluble, strongly basic lithium compounds in an inert solvent at reaction temperatures from 0.degree. to 200.degree. C.Type: GrantFiled: March 13, 1992Date of Patent: April 19, 1994Assignee: Metallgesellschaft AGInventors: Wilfried Weiss, Klaus Kobele
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Patent number: 5292732Abstract: The novel pyrrolopyrazines of the general formula ##STR1## wherein one of R.sup.1 and R.sup.2 signifies aryl and the other signifies hydrogen, lower alkyl or aryl or R.sup.1 and R.sup.2 together with the two carbon atoms denoted by .alpha. and .beta. signify the group A; ##STR2## R.sup.3 signifies hydrogen or lower alkyl and R.sup.4 signifies hydrogen orR.sup.3 and R.sup.4 together signify an additional C/N bond;R.sup.5 signifies hydrogen or lower alkyl;R.sup.6 signifies hydrogen or lower alkyl;R.sup.7 signifies hydrogen, halogen, lower alkyl, optionally substituted lower alkoxy, or C.sub.3-6 -cycloalkyl, C.sub.4-6 -cycloalkenyl, C.sub.Type: GrantFiled: June 26, 1992Date of Patent: March 8, 1994Assignee: Hoffmann-La Roche Inc.Inventor: Stephan Rover
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Patent number: 5292902Abstract: The invention concerns a process for the manufacture of a mixture of (3a.alpha.,5a.beta.,9a.alpha.,9b.beta.)-dodecahydro-3a,6,6,9a-tetramethyln aphtho-[2,1-b]furan and (3a.alpha.,5a.beta.,9a.alpha.,9b.alpha.)-dodecahydro-3a,6,6,9a-tetramethyl naphtho[2,1-b]furan which utilizes the substituted hexenoic acids, 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-2- or -3-enoic acid. The invention also concerns nitriles and a process for manufacture of the hexonic acids from the nitriles, having the formula ##STR1## wherein one of the bonds denotes a single bond and the other denotes a double bond, and, R represents hydrogen or the ester group COOR.sup.1 in which R.sup.1 represents a lower alkyl or aryl group.Type: GrantFiled: July 24, 1992Date of Patent: March 8, 1994Assignee: Givaudan-Roure CorporationInventor: Daniel Helmlinger
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Patent number: 5290955Abstract: (-)-2,5,5,8a-Tetramethyl-1-(carboxymethyl)-2-hydroxydecalin is subjected to lactonization by dehydration to form decahydro-3a,6,6,9a-tetramethyl(3a.alpha.,5a.beta.,9a.alpha.,9b.beta.)-(+) -naphtho[2,1-b]furan-2(1H)-one, which is then reduced with a metal hydride to convert it into (-)-2,5,5,8a-tetramethyl-1-(carboxymethyl)-2-hydroxydecalin, followed by dehydrative cyclization to give L-ambrox.The (-)-2,5,5,8a-tetramethyl-1-(carboxymethyl)-2-hydroxydecalin is produced from its racemic mixture. The resolution is performed using a 1-(aryl)ethylamine. The starting material for the synthesis is beta-ionone.Type: GrantFiled: December 23, 1992Date of Patent: March 1, 1994Assignee: Kuraray Co., Ltd.Inventors: Goro Asanuma, Yoshin Tamai
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Patent number: 5284870Abstract: The present invention relates to an aldose reductase inhibitor represented by the formula: ##STR1## wherein R.sub.1 is (CH.sub.2).sub.2 COOH and R.sub.2 is phenyl or p-hydroxyphenyl, or R.sub.1 and R.sub.2 are combined together to form a group of the formula: ##STR2## which was isolated from the fermentation products of Chaetomella circinoseta RF-3192.Type: GrantFiled: February 9, 1993Date of Patent: February 8, 1994Assignee: Shionogi Seiyaku Kabushiki KaishaInventors: Tadashi Yoshida, Toshiyuki Kato, Yoshimi Kawamura, Koichi Matsumoto, Hiroshi Itazaki
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Patent number: 5274134Abstract: The invention relates to a process for the stereo-selective preparation of 8.alpha.,12-oxido-13,14,15,16-tetranorlabdane by dehydration of 8.alpha.,12-dihydroxy-13,14,15,16-tetranorlabdane with acid-charged aluminium oxides.Type: GrantFiled: October 11, 1991Date of Patent: December 28, 1993Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Klaus Bruns, Theo Stalberg
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Patent number: 5268355Abstract: Compounds of formula ##STR1## having a double bond in one of the positions indicated by the dotted lines and wherein symbol R represents a hydrogen atom or a methyl radical, are useful ingredients for the preparation of perfuming compositions and perfumed articles, to which they impart odor notes of the woody-amber type.Type: GrantFiled: February 9, 1993Date of Patent: December 7, 1993Assignee: Firmenich S.A.Inventors: Roger L. Snowden, Sina D. Escher