Five-membered Alicyclic Ring Containing Patents (Class 568/379)
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Patent number: 5929291Abstract: The invention relates to compounds of the general formula ##STR1## in which R.sup.1 to R.sup.7 are, independently, H, methyl or ethyl, R.sup.8 +R.sup.9 together form methylene (--CH.sub.2 --) or a single bond, or R.sup.1 +R.sup.2 together form --(CH.sub.2).sub.n --, with n being 3 or 4, or R.sup.3 +R.sup.5 or R.sup.5 +R.sup.7 represent methylene or a single bond; and the presence of at least one cyclopropane ring in the molecule is compulsory and the side chain can be saturated or contains one double bond in position .alpha.,.beta. or .beta., .gamma. a process for the manufacture of these compounds, compounds used to perform the process and the use of these compounds as an odorant or as an ingredient of an odorant composition.Type: GrantFiled: April 9, 1997Date of Patent: July 27, 1999Assignee: Givaudan Roure (International) SAInventors: Jerzy A. Bajgrowicz, Georg Frater
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Patent number: 5874634Abstract: A halogenated substituted cyclopentene derivative of formula (I): ##STR1## wherein R is a hydrogen atom, alkyl radical having 1-6 carbon atoms, alkenyl radical having 2-6 carbon atoms, alkynyl radical having 2-6 carbon atoms, cycloalkyl radical having 3-8 carbon atoms, aralkyl radical having 7-19 carbon atoms, aryl radical having 6-12 carbon atoms, alkoxy radical having 1-6 carbon atoms, alkenyloxy radical having 2-6 carbon atoms, alkylthio radical having 1-6 carbon atoms or alkenylthio radical having 2-6 carbon atoms; X.sup.1 is (.alpha.-OZ.sup.a, .beta.-H) or (.alpha.-H, .beta.-OZ.sup.a), X.sup.3 is (.alpha.-OZ.sup.d, .beta.-H), (.alpha.-H, .beta.-OZ.sup.d) or oxygen atom, each of Z.sup.a and Z.sup.d, which may be the same or different, is a hydrogen atom or a protective radical for a hydroxyl radical; and W is a halogen atom.Type: GrantFiled: September 2, 1997Date of Patent: February 23, 1999Assignees: Nissan Chemical Industries, Ltd., Fumie SatoInventor: Fumie Sato
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Patent number: 5866497Abstract: A catalyst precursor of the formula: ##STR1## wherein: R.sup.1 is a cycloalkadienyl ligand;R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are independently hydrogen, a hydrocarbyl group containing 1 to 20 carbon atoms, or a silyl group, and may be connected to R.sup.1 through a bridging group comprising at least two Group IVA atoms; with the proviso that one of R.sup.3, R.sup.4, and R.sup.5 is a negative charge stabilizing group selected from the group consisting of Group IVA trialkyl groups, aryl groups, heteroaromatic groups, ethylenically unsaturated hydrocarbon groups, acetylenically unsaturated hydrocarbon groups, ketonic groups, and aromatic organometallic moieties, is provided. When combined with a compound comprising a metal from Groups IIIB to VIII or the Lanthanide series of the Periodic Table of elements and an activating cocatalyst, the catalyst precursor is useful for the polymerization of olefins.Type: GrantFiled: June 26, 1997Date of Patent: February 2, 1999Assignee: Univation Technologies LLCInventor: Rex Eugene Murray
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Patent number: 5856582Abstract: A process for the manufacture of 2-hydroxy-3-methylcyclopent-2-ene-1-one, in which an ester of alpha-methyl glutaric acid and an ester of oxalic acid react in a polar aprotic solvent in the presence of an alkali metal alkoxide to form an intermediate compound which, after removal of said polar aprotic solvent and alcohols formed in the reaction, is hydrolyzed and decarboxylated to form said 2-hydroxy-3-methycyclopent-2-ene-1-one.Type: GrantFiled: September 26, 1997Date of Patent: January 5, 1999Inventor: Glen Francis Crum
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Patent number: 5808112Abstract: The present invention relates to a novel process for preparing cis-4-O-protected-substituted-2-cyclopentenol derivatives comprising, a) dissolving a 4-O-protected-2-cyclopentenone in a suitable organic solvent; and b) treating the solution with a suitable Lewis acid and a suitable reducing agent at a temperature of from about -100.degree. C. to about 20.degree. C. The cis-4-O-protected-substituted-2-cyclopentenol derivatives are useful intermediates in the preparation of various cyclopentanyl and cyclopentenyl purine analogs which are useful as immunosuppressants and in the preparation of various prostaglandins.Type: GrantFiled: June 17, 1997Date of Patent: September 15, 1998Assignee: Hoechst Marion Roussel Inc.Inventors: Timothy T. Curran, David A. Hay, Jonathan C. Evans
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Patent number: 5763664Abstract: A process for preparing a cyclopentenone by forming a two-phase mixture of a 1,4-diketone, a water immiscible organic solvent, and an aqueous base solution, and heating the mixture so as to convert the 1,4-diketone to a cyclopentenone which collects in the organic solvent phase.Type: GrantFiled: December 1, 1995Date of Patent: June 9, 1998Assignee: Albemarle CorporationInventor: Paul C. Saunders
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Patent number: 5760277Abstract: The cycloaliphatic ketones of formula ##STR1## having two conjugated double bonds in positions 1 and 3, or 2 and 4, such as indicated by the dotted lines, and wherein R defines a C.sub.1 to C.sub.Type: GrantFiled: January 15, 1997Date of Patent: June 2, 1998Assignee: Firmenich SAInventors: Ferdinand Naef, Rene Decorzant
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Patent number: 5646098Abstract: The invention relates to novel compositions comprising ene and free radical adducts of unsaturated and saturated hydrocarbons, and acyclic and cyclic vicinal polycarbonyl compounds such as diethyl ketomalonate and indantrione. The adducts are reacted with nucleophiles such as amines, electrophiles such as anhydrides and esters, and metal ions. Post-products are obtained via reaction of said products with capping reagents such as boric acid. Compositions containing said adducts, products and post-products include oleaginous substances such as fuels and lube oils.Type: GrantFiled: May 13, 1994Date of Patent: July 8, 1997Assignee: Exxon Chemical Patents IncInventor: Stanley J. Brois
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Patent number: 5597938Abstract: A novel process for the production of a compound represented by the formula: ##STR1## wherein Z and Z' each represents a protective group for the hydroxyl group; R.sup.1 represents a hydrogen atom or an alkyl group; R.sup.2 represents an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a group represented by the formula --B--D (in which B is an alkylene group and D is a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenoxy group or a cycloalkyl group), a substituted or unsubstituted phenyl group or a substituted or unsubstituted phenoxy group; R.sup.3 and R.sup.4 each represents a hydrogen atom, an alkyl group or an alkoxy group; R.sup.5 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a cyano group, an amino group, a hydroxyl group or a group represented by a formula --COOR.sup.8 ; R.sup.6 represents a group represented by a formula --COOR.sup.9, a cyano group, a hydroxyl group, a group represented by a formula --OCOR.sup.Type: GrantFiled: August 10, 1995Date of Patent: January 28, 1997Assignees: Taisho Pharmaceutical Co., Ltd., Fumie SatoInventor: Fumie Sato
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Patent number: 5583262Abstract: The present invention is directed to solid salts of hop acids and to processes for their production. Preferred are solid sodium and potassium salts of isoalpha acids rho-isoalpha acids, tetrahydroisoalpha acids, hexahydroisoalpha acids and beta acids.Type: GrantFiled: November 10, 1994Date of Patent: December 10, 1996Inventors: John P. Maye, Scot W. Weis
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Patent number: 5519160Abstract: Derivatives of alkyl 3-(substituted or unsubstituted benzylidene)-1-alkyl-2-oxocylopentanecarboxylate of the following formula (I), ##STR1## wherein R.sup.1 and R.sup.2 individually represent a lower alkyl group; X is a halogen atom, a cyano group, an alkyl group, a haloalkyl group, a phenyl group, or a nitro group; and m is an integer of 0 to 5; provided when m is 2 or larger, Xs may be either the same or different. The compounds are useful themselves as an effective ingredient of antifungal compositions, and can be used for intermediates of agriculture chemicals and medicines.Type: GrantFiled: November 15, 1994Date of Patent: May 21, 1996Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Heitaro Obara, Satoru Kumazawa
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Patent number: 5512543Abstract: The chiral isomers of 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol and, more particularly, the (-)-(1'R,2S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4- penten-2-ol and (+)-(1'S,2S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4- penten-2-ol, are useful as perfuming ingredients to impart sandalwood type odor notes to the perfuming compositions and perfumed articles into which they are incorporated.Type: GrantFiled: August 2, 1994Date of Patent: April 30, 1996Assignee: Firmenich S.A.Inventors: Christian Chapuis, Antoine Gautier, Pierre-Alain Blanc
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Patent number: 5504066Abstract: The invention concerns pentene derivatives of the general formula (I), in which, independently of each other, R.sup.1 is hydrogen or a methyl group, R.sup.2 and R.sup.3 are hydrogen or an alkyl group with 1 to 5 C-atoms, R.sup.4 is hydrogen or a CHR.sup.5 R.sup.6 group (R.sup.5 and R.sup.6 being hydrogen or an alkyl group with 1 to 6 C-atoms) and X is a CO or CHOH group, with the provision that (a) at least one of the groups R.sup.2 and R.sup.3 is an alkyl group and (b) 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-1-ol is excluded. Such compounds are odoriferous substances with interesting fragrances and high diffusion power.Type: GrantFiled: October 18, 1994Date of Patent: April 2, 1996Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Thomas Markert, Volker Porrmann, Klaus Bruns
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Patent number: 5500156Abstract: Compositions for use in non-linear optical devices. The compositions have first molecular electronic hyperpolarizability (.beta.) either positive or negative in sign and therefore display second order non-linear optical properties when incorporated into non-linear optical devices.Type: GrantFiled: April 11, 1994Date of Patent: March 19, 1996Assignee: California Institute of TechnologyInventors: Seth R. Marder, Chin-Ti Chen, Lap-Tak Cheng
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Patent number: 5498734Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.Type: GrantFiled: July 30, 1993Date of Patent: March 12, 1996Assignee: University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5468880Abstract: Improvement in the technique of synthesizing prostaglandins, particularly those having at least one halogen atom at the 16- or 17-position, which comprises introducing a .omega. chain into the aldehyde thereby to enable considerable yield improvement in the production of .alpha.,.beta.-unsaturated ketones, and which does not involve hydrogen generation and can insure safe operation.A method of producing .alpha.,.beta.-unsaturated ketones by reacting aldehyde with 2-oxoalkyl phosphonate, wherein the reaction was carried out under the presence of a base and a zinc compound.Type: GrantFiled: May 31, 1994Date of Patent: November 21, 1995Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuji Ueno, Tomio Oda
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Patent number: 5407910Abstract: The present invention provides novel compounds such as 1,2-dimethyl-4-butyl-cyclopent-1-en-3,5-dione and 1,2-dimethyl-4,4-dibutyl-cyclopent-1-en-3,5-dione, having active floral-type aroma and methods for preparing same.Type: GrantFiled: October 12, 1993Date of Patent: April 18, 1995Assignee: Union Camp CorporationInventors: Benjamin O. Isaac, Chat O. Chan, Ian M. Marr
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Patent number: 5405550Abstract: Molecular bulding beams, liquid crystals, and surfactants in the form of compounds based on [1.1.1]propellane, including poly[1.1.1]propellanes. Molecular building beams having a telomeric or polymeric chain staff, and linking groups functionalized on one or both ends of the staff. A system for linking the beams to connecting units to construct molecular structures of various forms, such as whips, combs, scaffoldings, nets, or stars. Other broad aspects of the invention provide liquid crystals and surfactants. The liquid crystals include telomeric or polymeric compounds functionalized with flexible end groups, while the surfactant compounds are functionalized with surface active end groups. Methods of synthesizing the various compounds ar also provided.Type: GrantFiled: August 10, 1992Date of Patent: April 11, 1995Assignee: Josef MichlInventors: Josef Michl, Piotr Kaszynski, Andrienne C. Friedli
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Patent number: 5395977Abstract: A process for producing optically active 4-hydroxy-2-cyclopentenone [1] which comprises reacting 4-hydroxy-2-cyclopentenone represented by the formula: ##STR1## with an optically active propargyl alcohol derivative represented by the general formula: ##STR2## wherein R and R.sup.1 each independently represent a halogenated phenyl group, an alkylphenyl group, or an alkyl group which may be substituted with one or more halogen atom(s), and * indicates an asymmetric carbon atom, to form an optically active complex [3] consisting essentially of optically active 4-hydroxy-2-cyclopentenone represented by the formula [1] ##STR3## wherein * indicates an asymmetric carbon atom, and the optically active propargyl alcohol derivative [2], and then decomposing the optically active complex [3].Type: GrantFiled: March 12, 1993Date of Patent: March 7, 1995Assignee: Sumitomo Chemical Company, Ltd.Inventors: Fumio Toda, Yorihiko Inoue, Masayoshi Minai
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Patent number: 5288811Abstract: Accordingly, novel carbonyl containing compositions are prepared by contacting, in the presence of a free radical initiator, a compound selected from the group consisting of saturated hydrocarbons, substituted saturated hydrocarbons, polymers and mixtures thereof with a carbonyl containing compound or mixtures thereof having the structures: ##STR1## wherein Q.dbd.HOH, MeOH, EtOH, or n-BuOH; n.dbd.0,1,>; and X and Y are independently selected from the group consisting of CH.sub.2, C.dbd.O; W is independently selected from the group consisting of CH.sub.2, C.dbd.O, O, NH, CMe.sub.2, C.dbd.N-alkyl and N-alkyl, wherein alkyl is 1 to 18 carbons; U and V are independently selected from the same groups as W and dependently selected so that U and V taken together are one of 1,2-phenylene, 1,8-naphthalene-diyl, and 1,2-naphthalene-diyl.Type: GrantFiled: November 5, 1992Date of Patent: February 22, 1994Assignee: Exxon Research and Engineering CompanyInventor: Stanley J. Brois
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Patent number: 5288701Abstract: The invention concerns novel odorants, namely derivatives of dihydrocampholenic aldehyde having the formula ##STR1## wherein R is ##STR2## one of the dotted lines in each of (a) and (b) represents an additional bond, and,R.sup.1, R.sup.2 and R.sup.3 are selected from the group consisting of hydrogen and alkyl groups of from one to four carbon atoms, with the proviso that R.sup.3 is present only when the additional bond is between the carbon atoms designated as .beta. and .gamma..The invention also concerns odorant compositions containing the dihydrocampholenic aldehyde derivatives and methods for making same.Type: GrantFiled: July 1, 1991Date of Patent: February 22, 1994Assignee: Givaudan-Roure CorporationInventor: Josianne Baudin
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Patent number: 5276199Abstract: A process for preparing a cyclopentenone by forming a two-phase mixture of a 1,4-diketone, a water immiscible organic solvent, and an aqueous base solution, and heating the mixture so as to convert the 1,4-diketone to a cyclopentenone which collects in the organic solvent phase.Type: GrantFiled: February 11, 1993Date of Patent: January 4, 1994Assignee: Ethyl CorporationInventors: John Y. Lee, Meng-Sheng Ao, Stephen E. Belmont
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Patent number: 5180844Abstract: The present invention provides an optically active 2-methylenecyclopentanone derivative represented by the general formula ##STR1## (wherein R.sup.1 is a protective group for hydroxyl, and the symbol * represents an asymmetric carbon atom).Type: GrantFiled: July 9, 1991Date of Patent: January 19, 1993Assignee: Daiso Co., Ltd.Inventors: Takashi Takahashi, Yoshikazu Takehira
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Patent number: 5149711Abstract: A 2-cyclopentenone derivative represented by the following formula ##STR1## wherein R.sup.1 represents an alkyl group having 1 to 10 carbon atoms which may be substituted by a substituted or unsubstituted phenyl or phenoxy group, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and each represents a hydrogen atom or a lower alkanoyl group, and the wavy line shows that the bonded state of the double bond is E or Z.This compound is useful for treating, for instance, malignant tumors.Type: GrantFiled: March 7, 1989Date of Patent: September 22, 1992Assignee: Teijin LimitedInventors: Atsuo Hazato, Seizi Kurozumi
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Patent number: 5149843Abstract: Conjugated diene compounds of the general formula: ##STR1## which are industrially advantageous intermediates for preparing sarcophytol A useful as an anticarcinogenic promotor or antitumor agent are provided.Type: GrantFiled: June 7, 1991Date of Patent: September 22, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5075478Abstract: A process for preparing prostaglandin derivatives by reacting a trans bis-tin ethylene with an organo metal compound then with a compound selected from an epoxide, aldehyde, or ketone, then, without isolation and in the same reaction vessel, reacting with an organo lithium compound, a cuprate complex and a cyclopentenone to produce a prostaglandin intermediate having an unprotected hydroxyl group on the omega side chain.Type: GrantFiled: January 17, 1991Date of Patent: December 24, 1991Assignee: G. D. Searle & Co.Inventors: James R. Behling, John R. Medich
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Patent number: 4992577Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.Type: GrantFiled: May 22, 1989Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4981872Abstract: Prostaglandin derivatives having an oxo group at specified positions in the .alpha. side chain have a variety of physiological effects, notably a strong anti-ulcer activity accompanied by a limited ability to inhibit blood platelet aggregation.Type: GrantFiled: January 15, 1988Date of Patent: January 1, 1991Assignee: Sankyo Company LimitedInventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Keiichi Tabata, Nobuyoshi Iwata
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Patent number: 4942256Abstract: This invention relates to several novel intermediates useful in the manufacture of thromboxane A.sub.2 inhibiting 7-[3-.alpha.-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-bicyclo[2.2. 1]-heptenoic acids.Type: GrantFiled: December 13, 1988Date of Patent: July 17, 1990Assignee: National Research Development CorporationInventors: Robert B. Garland, Masateru Miyano
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Patent number: 4921995Abstract: A novel process for manufacturing 16-substituted .DELTA..sup.7 -prostaglandin Es, which include compounds expressed by the following formula (I), their enanantiomers, or their mixtures of arbitrary mixing ratio, ##STR1## wherein R.sup.1 indicates COOR.sup.2, CH.sub.2 OR.sup.3, or COCH.sub.2 OR.sup.3, in which R.sup.2 indicates a hydrogen atom, a substituted or unsubstituted C.sub.1 -C.sub.10 alkyl group, a substituted or unsubstituted C.sub.3 -C.sub.10 cycloalkyl group, or a substituted or unsubstituted phenyl group, and R.sup.3 indicates a hydrogen atom, a tri(C.sub.1 -C.sub.7) hydrocarbon silyl group, a group which forms an acetal bond together with the oxygen atom of a hydroxyl group, or a C.sub.2 -C.sub.7 acyl group; R.sup.4 and R.sup.5 are identical or different, each representing a hydrogen atom, a tri(C.sub.1 -C.sub.7) hydrocarbon silyl group, or a group which forms an acetal bond together with the oxygen atom of a hydroxyl group; R.sup.6 indicates a hydrogen atom, a C.sub.1 -C.sub.Type: GrantFiled: February 9, 1988Date of Patent: May 1, 1990Assignee: Teijin LimitedInventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi, Masahiro Koga
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Patent number: 4904640Abstract: 2-Alkylidene-3,3,5(3,5,5)-trimethylcyclopentanones corresponding to the following general formula ##STR1## in which three of the substituents R.sub.1 to R.sub.4 are CH.sub.3, one of the substituents R.sub.1 to R.sub.4 is H, and R.sub.5 is a saturated or unsaturated, linear branched C.sub.1 -C.sub.7 alkyl radical, and the double bond is in the endo position to the cyclopentanone structure. The compounds of formula (I) are useful as perfumes.Type: GrantFiled: March 4, 1988Date of Patent: February 27, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Thomas Markert, Klaus Bruns, Horst-Juergen Krause, Josef Penninger, Michael Virnig, Volker Falk
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Patent number: 4894483Abstract: Vinylglyoxal derivatives of the general formula I ##STR1## where R is straight-chain or branched alkyl or alkenyl, cycloalkyl or unsubstituted or substituted phenyl, are prepared by a process in which bicyclo[2.2.1]hept-5-enecarbaldehyde of the formula V ##STR2## is either (a) subjected to autocondensation with formation of a compound of the formula VII ##STR3## or (b) reacted with a compound of the general formula IIR-CH.dbd.O (II)where R has the above meanings, with formation of a mixture of the compounds of the general formulae VIII (a) and (b) ##STR4## where R is as defined above, in the presence of a catalyst, and the compound of the formula VII or the compounds of the formulae VIII (a) and (b) is or are oxidized to the corresponding dicarbonyl compounds, after which gas-phase pyrolysis is carried out at from 500.degree. to 700.degree. C. and under reduced pressure, in particular less than 10.sup.-1 mbar, and, if desired, the resulting compound of the general formula I is further purified.Type: GrantFiled: October 28, 1987Date of Patent: January 16, 1990Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Hans-Dieter Martin, Roland Kramme, Ralf T. Weimann
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Patent number: 4892966Abstract: The invention is concerned with a novel process for the manufacture of compounds of the formula ##STR1## wherein R.sup.1 signifies C.sub.1-5 -alkyl, especially methyl, ethyl, propyl or isopropyl, and the radicals R.sup.2 each independently represent hydrogen or C.sub.1-5 -alkyl, especially hydrogen or methyl, ethyl, propyl or isopropyl.The process is characterized in that a compound of the formula ##STR2## wherein R stands for C.sub.1-4 -alkoxy, chlorine, bromine or C.sub.1-4 -alkanoyloxy, R.sup.1 and R.sup.2 have the above significance and R.sup.3 represents C.sub.1-4 -alkyl.is hydrolyzed and subjected to an aldol condensation and, where R=C.sub.1-4 -alkoxy, the reaction product is subsequently subjected to an acid treatment.The compounds I are for the most part known flavoring substances.Type: GrantFiled: July 16, 1987Date of Patent: January 9, 1990Assignee: Givaudan CorporationInventor: Hans J. Wild
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Patent number: 4847370Abstract: Compounds are described of formula ##STR1## wherein n is 1 or 2;m is 2-5 and X is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --; or m is 1-4 and x is --CH.dbd.C.dbd.CH--;Z is --CH.sub.2 OH, --CHO or --CONHR.sup.1 [where R.sup.1 is a hydrogen atom or C.sub.1-4 alkyl, aryl, --COR.sup.2 (where R.sup.2 is a hydrogen atom or a C.sub.1-4 alkyl or aryl group) or --SO.sub.2 R.sup.3 (where R.sup.3 is a C.sub.1-4 alkyl or aryl group)];Y is substituted or unsubstituted 3-phenoxy-2-hydroxypropyl.These compounds inhibit gastric acid secretion and provide gastrointestinal cytoprotection, and may be formulated for use in the treatment of ulcers.Type: GrantFiled: October 21, 1987Date of Patent: July 11, 1989Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Harry Finch, Duncan B. Judd, James D. Meadows
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Patent number: 4756764Abstract: 3,10-Diacetyl-11-isopropylidene-7,7-dimethyl-tricyclo[6.2.1.0.sup.2,6 ]undeca-2,5,9-triene is a flavoring ingredient useful for the aromatization of smoking articles. It develops upon smoking green, slightly floral, metallic, astringent, fatty, slightly bitter and earthy notes.It is prepared by a two-step process from 1-(4-isopropylidene-1-cyclopent-1-enyl)-1-ethanone.Type: GrantFiled: February 26, 1987Date of Patent: July 12, 1988Assignee: Firmenich SAInventors: Alan F. Thomas, Alistair Y. Smith
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4-hydroxy-2-cyclopentenone, process for production thereof, pharmaceutical composition comprising it
Patent number: 4711895Abstract: A 4-hydroxy-2-cyclopentenone represented by the following formula (I) ##STR1## wherein X represents a hydrogen or halogen atom, A represents a hydrogen atom and B represents a hydroxyl group, or A and B are bonded to each other to represent a bond, R.sup.1 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 10 carbon atoms, R.sup.2 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 10 carbon atoms, and R.sup.3 represents a hydrogen atom or a protective group for a hydroxyl group, provided that R.sup.2 is not a 2-octenyl, 8-acetoxy-2-octenyl or 2,5-octadienyl group. The compounds of formula (I) in which A is hydrogen and B is hydroxyl group are prepared by subjecting a 5-unsubstituted cyclopentenone and an aldehyde to aldol condensation reaction. The compounds of formula (I) in which A and B form a bond is prepared by subjecting the compounds of the formula (I) in which A is hydrogen and B is hydroxyl group to dehydration.Type: GrantFiled: October 22, 1985Date of Patent: December 8, 1987Assignee: Teijin LimitedInventors: Atsuo Hazato, Satsohi Sugiura, Seizi Kurozumi, Ryoji Noyori -
Patent number: 4703127Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sup.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight- or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y and R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.Type: GrantFiled: September 2, 1983Date of Patent: October 27, 1987Assignee: The Australian National UniversityInventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
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Patent number: 4696944Abstract: A compound of formula I ##STR1## in which formula: R.sub.a represents hydrogen or a C.sub.1 -C.sub.6 alkyl group, and R.sub.c represents a C.sub.1 -C.sub.6 alkyl group;R.sub.b represents a phenyl group, optionally substituted by a C.sub.1 -C.sub.6 alkyl group or halogen, a group of formula --CH.dbd.CR.sub.d R.sub.e in which R.sub.d and R.sub.e, which may be identical or different represent hydrogen or C.sub.1 -C.sub.6 alkyl groups or a group of formula --CH.dbd.NOR.sub.f in which R.sub.f represents hydrogen or a C.sub.1 -C.sub.6 alkyl group andRCOO represents a residue of an acid RCO.sub.2 H, which acid, or an ester-forming derivative of which acid, on reaction with .alpha.-cyano-3-phenoxybenzyl alcohol or an ester forming derivative thereof, gives rise to an .alpha.-cyano-3-phenoxybenzyl ester having pesticidal properties.Type: GrantFiled: March 14, 1985Date of Patent: September 29, 1987Assignee: National Research Development CorporationInventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay
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Patent number: 4693845Abstract: Novel bornane-3-spiro-1'-cylopentane derivatives of the following formula (I) ##STR1## in which R.sub.1 and R.sub.2 are defined such that when R.sub.1 is a hydrogen atom, R.sub.2 is a hydroxyl group, or R.sub.1 and R.sub.2 are joined to form a ketone are obtained from camphor.The derivatives are synthesized in a simple process from an economical starting material, camphor. The derivatives have woody-note and can be widely used in perfumes, soaps, shampoos, hair rinses, cosmetics and the like.Type: GrantFiled: June 18, 1986Date of Patent: September 15, 1987Assignee: KAO CorporationInventors: Yoshiaki Fujikura, Akira Yamamuro, Motoki Nakajima
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Patent number: 4668828Abstract: A method for oligomerization of a group of prostaglandin analogs such as Ethyl Analog 3-(trans-3-keto-1-pentenyl)-2-ethyl-2-cyclopentenone into a biologically active exhibiting protection of oxidative phosphorylation of degenerated mitochondria and sodium bicarbonate soluble oligomeric mixtures is described. The Ethyl Analog is treated with ethanolic potassium hydroxide solution with exposure to atmospheric oxygen at moderate conditions of temperature, time and concentration.Type: GrantFiled: May 6, 1983Date of Patent: May 26, 1987Assignee: The United States of America as represented by the Secretary of the NavyInventor: George L. Nelson
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Patent number: 4663486Abstract: A method for oligomerization of a group of prostaglandin analogs such as Ethyl Analog 3-(trans-3-keto-1-pentenyl)-2-ethyl-2-cyclopentenone into a biologically active exhibiting protection of oxidative phosphorylation of degenerated mitochondria and sodium bicarbonate insoluble oligomeric mixtures is described. The Ethyl Analog is treated with ethanolic potassium hydroxide solution in an oxygen-free atomsphere at moderate conditions of temperature, time and concentration.Type: GrantFiled: May 6, 1983Date of Patent: May 5, 1987Assignee: The United States of America as represented by the Secretary of the NavyInventor: George L. Nelson
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Patent number: 4661641Abstract: Compounds of the formula ##STR1## wherein n is either 0 or 1; R.sup.1 and R.sup.2 is hydrogen and the other is hydrogen, hydroxy, oxo group, a protected hydroxy or protected oxo group; R.sup.3 is hydroxy oxo group, .dbd.CH--CH.sub.2 --OH, .dbd.CH--CHO or one of the foregoing groups where the hydroxy or oxo functions are protected; R.sup.4 is --CO--OR.sup.6, --CO--R.sup.6, --CO--NR.sup.6 R.sup.7, --CO--Cl or --SO.sub.2 --R.sup.6 ; R.sup.6 is saturated or aromatic hydrocarbon; and R.sup.7 is saturated or aromatic hydrocarbon or hydrogen,are converted by cleavage of R.sup.4 OH into corresponding cycloalkenes and protecting groups, if present, are hydrolyzed.The compounds obtained are valuable intermediates in carotenoid syntheses.Type: GrantFiled: May 29, 1984Date of Patent: April 28, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
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Patent number: 4625066Abstract: Novel substituted acetylene-ketones of the formulaR.sup.2 --C.tbd.C--CO--R.sup.1 (I)in whichR.sup.1 represents optionally substituted cycloalkyl with 4 to 7 carbon atoms or the groupings ##STR1## or represents optionally substituted aryl, if R.sup.2 represents optionally substituted cycloalkenyl or optionally substituted cycloalkylalkyl;R.sup.2 represents alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkylalkyl, optionally substituted aryl or optionally substituted aralkyl;R.sup.3 represents halogen;R.sup.4 represents hydrogen or halogen;R.sup.5 represents alkyl with more than 1 carbon atom, alkenyl, alkinyl or the CHO group or a derivative thereof, or represents methyl, if R.sup.2 represents optionally substituted cycloalkenyl or optionally substituted cycloalkylalkyl;R.sup.6 represents cyano, optionally substituted aryl or the groupings --XR.sup.7 or --CONR.sup.8 R.sup.9 ;R.sup.Type: GrantFiled: November 29, 1984Date of Patent: November 25, 1986Assignee: Bayer AktiengesellschaftInventor: Hans-Ludwig Elbe
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Patent number: 4622410Abstract: The present invention relates to intermediates of the general formula: ##STR1## (wherein Y and Z, which may be the same or different, each represents a trans-vinylene group or an ethylene group, R.sup.2 represents a hydrogen atom or a methyl or ethyl group, R.sup.3 represents a single bond or an alkylene group of 1 to 5 carbon atoms, R.sup.4 represents an alkyl group of 1 to 8 carbon atoms, a cycloalkyl group of 4 to 7 carbon atoms unsubstituted or substituted by at least one alkyl group of 1 to 8 carbon atoms or a phenyl or phenoxy group unsubstituted or substituted by at least one halogen atom, trifluoromethyl group or alkyl group of 1 to 4 carbon atoms, R.sup.5 represents a hydroxy- protecting group which can be removed in acidic conditions and W.sup.1 represents a group of the formula: --COOR.sup.1, --CON(R.sup.6).sub.2, --CH.sub.2 OR.sup.5 or --CH(OR.sup.7)CH.sub.2 OR.sup.5 (in which R.sup.1 represents a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, the groups R.sup.Type: GrantFiled: March 18, 1985Date of Patent: November 11, 1986Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Nobuyuki Hamanaka, Hideo Takada, Yoshinobu Arai
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Patent number: 4618687Abstract: A cyclopentenone compound represented by the following formula: ##STR1## has an antitumor effect and can be produced from the antibiotic XK-213.Type: GrantFiled: April 18, 1985Date of Patent: October 21, 1986Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Tadashi Hirata, Hiromitsu Saito, Makoto Morimoto
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Patent number: 4612308Abstract: The syntheses of 25,26-dehydro-1.alpha.,23S-dihydroxycholecalciferol, 25,26-dehydro-1.alpha.,23R-dihydroxycholecalciferol, and the epimeric mixture thereof which are useful as differentiation inducing agents and anti-proliferation agents are described, 25,26-dehydro-1.alpha.,23S-dihydroxycholecalciferol 25,26-dehydro-1.alpha.,23R-dihydroxycholecalciferol and the epimeric mixture thereof are useful for treating tumors and leukemia, and osteoporosis.Type: GrantFiled: November 29, 1984Date of Patent: September 16, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Enrico G. Baggiolini, Gary A. Truitt, Milan R. Uskokovic, Peter M. Wovkulich
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Patent number: 4576962Abstract: The 13,14-didehydro-15-oxo analogues of natural prostaglandins possess high cytoprotective activity and low diarrheogenic activity, low anti-hemostatic activity and low smooth muscle contraction activity.Type: GrantFiled: May 4, 1984Date of Patent: March 18, 1986Assignee: The Procter & Gamble CompanyInventor: Randall S. Matthews
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Patent number: 4571345Abstract: Compounds of the formula: ##STR1## wherein n is 0 or 1, R is lower alkyl (substituted or unsubstituted), R' is H or lower alkyl, and R" is a branched alkyl, alkyl-cycloalkyl, cycloalkyl, polycycloalkyl (poly=2 or more, fused or non-fused), phenyl or alkyl-substituted phenyl, and physiologically acceptable cationic and acid addition salts thereof, which compounds are potent sweeteners. These derivatives of gem-diaminoalkanes are many times sweeter than sugar and are free from undesirable flavor qualities. Furthermore, they possess an unanticipated high degree of solubility compared with known synthetic sweeteners. In addition, the compounds possess high stability so that they can be used in all types of beverages and in conventional food processing. Sweetening compositions and sweetened edible compositions of these compounds are also provided.Type: GrantFiled: June 13, 1983Date of Patent: February 18, 1986Assignee: Cumberland Packing Corp.Inventors: Michael S. Verlander, William D. Fuller, Murray Goodman
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Patent number: 4567004Abstract: Monomethyl-substituted methylene compounds are obtained by reacting methylene compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent --CN, --CO--R.sup.3, --SO.sub.2 --R.sup.3 or --NO.sub.2 andR.sup.1 can additionally denote -aryl(R.sup.1).sub.n,whereinR.sup.3 denotes --OH, alkyl, aralkyl, aryl, alkoxy, aralkoxy or aryloxy, or amino which is substituted by alkyl and/or aralkyl and/or aryl, and furthermoretwo radicals R.sup.3 together can be an alkylene group, the radical of an aliphatic diol or of an aliphatic diamine or the group --NH--CO--NH-- and n represents 1, 2 or 3,with formaldehyde and with hydrogen in the presence of a condensation catalyst and a hydrogenation catalyst at elevated temperature, the methylene compound being introduced into the liquid phase of the mixture of reactants in the course of the reaction.Type: GrantFiled: July 18, 1984Date of Patent: January 28, 1986Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Erich Wolters
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Patent number: 4543421Abstract: An improved method for the preparation of prostaglandin analogs which comprises preparation of two equivalents of an alkyl or alkenyl lithium reagent in an aprotic solvent mixture such as pentane or hexane and tetrahydrofuran, conversion of said reagent by addition of 1 equivalent of copper (I) cyanide to a copper reagent, conversion of said copper reagent to the blocked prostaglandin analog by the addition of a 2-alkylcyclopent-2-en-1-one reagent and quenching of the resultant reaction mixture with aprotic media or an active acylating agent and finally optionally deblocking the resultant product is disclosed. This method is an improvement over previous methods in that more modest temperatures and less hazardous and/or less complex reagents are used and in that for some analogs the method is shorter than previous methods.Type: GrantFiled: May 11, 1983Date of Patent: September 24, 1985Assignee: Miles Laboratories, Inc.Inventors: Paul F. Corey, Harold C. Kluender