Five-membered Alicyclic Ring Containing Patents (Class 568/379)
  • Patent number: 5929291
    Abstract: 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: Grant
    Filed: April 9, 1997
    Date of Patent: July 27, 1999
    Assignee: Givaudan Roure (International) SA
    Inventors: Jerzy A. Bajgrowicz, Georg Frater
  • Patent number: 5874634
    Abstract: 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: Grant
    Filed: September 2, 1997
    Date of Patent: February 23, 1999
    Assignees: Nissan Chemical Industries, Ltd., Fumie Sato
    Inventor: Fumie Sato
  • Patent number: 5866497
    Abstract: 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: Grant
    Filed: June 26, 1997
    Date of Patent: February 2, 1999
    Assignee: Univation Technologies LLC
    Inventor: Rex Eugene Murray
  • Patent number: 5856582
    Abstract: 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: Grant
    Filed: September 26, 1997
    Date of Patent: January 5, 1999
    Inventor: Glen Francis Crum
  • Patent number: 5808112
    Abstract: 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: Grant
    Filed: June 17, 1997
    Date of Patent: September 15, 1998
    Assignee: Hoechst Marion Roussel Inc.
    Inventors: Timothy T. Curran, David A. Hay, Jonathan C. Evans
  • Patent number: 5763664
    Abstract: 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: Grant
    Filed: December 1, 1995
    Date of Patent: June 9, 1998
    Assignee: Albemarle Corporation
    Inventor: Paul C. Saunders
  • Patent number: 5760277
    Abstract: 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: Grant
    Filed: January 15, 1997
    Date of Patent: June 2, 1998
    Assignee: Firmenich SA
    Inventors: Ferdinand Naef, Rene Decorzant
  • Patent number: 5646098
    Abstract: 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: Grant
    Filed: May 13, 1994
    Date of Patent: July 8, 1997
    Assignee: Exxon Chemical Patents Inc
    Inventor: Stanley J. Brois
  • Patent number: 5597938
    Abstract: 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: Grant
    Filed: August 10, 1995
    Date of Patent: January 28, 1997
    Assignees: Taisho Pharmaceutical Co., Ltd., Fumie Sato
    Inventor: Fumie Sato
  • Patent number: 5583262
    Abstract: 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: Grant
    Filed: November 10, 1994
    Date of Patent: December 10, 1996
    Inventors: John P. Maye, Scot W. Weis
  • Patent number: 5519160
    Abstract: 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: Grant
    Filed: November 15, 1994
    Date of Patent: May 21, 1996
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Heitaro Obara, Satoru Kumazawa
  • Patent number: 5512543
    Abstract: 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: Grant
    Filed: August 2, 1994
    Date of Patent: April 30, 1996
    Assignee: Firmenich S.A.
    Inventors: Christian Chapuis, Antoine Gautier, Pierre-Alain Blanc
  • Patent number: 5504066
    Abstract: 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: Grant
    Filed: October 18, 1994
    Date of Patent: April 2, 1996
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Thomas Markert, Volker Porrmann, Klaus Bruns
  • Patent number: 5500156
    Abstract: 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: Grant
    Filed: April 11, 1994
    Date of Patent: March 19, 1996
    Assignee: California Institute of Technology
    Inventors: Seth R. Marder, Chin-Ti Chen, Lap-Tak Cheng
  • Patent number: 5498734
    Abstract: 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: Grant
    Filed: July 30, 1993
    Date of Patent: March 12, 1996
    Assignee: University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5468880
    Abstract: 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: Grant
    Filed: May 31, 1994
    Date of Patent: November 21, 1995
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuji Ueno, Tomio Oda
  • Patent number: 5407910
    Abstract: 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: Grant
    Filed: October 12, 1993
    Date of Patent: April 18, 1995
    Assignee: Union Camp Corporation
    Inventors: Benjamin O. Isaac, Chat O. Chan, Ian M. Marr
  • Patent number: 5405550
    Abstract: 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: Grant
    Filed: August 10, 1992
    Date of Patent: April 11, 1995
    Assignee: Josef Michl
    Inventors: Josef Michl, Piotr Kaszynski, Andrienne C. Friedli
  • Patent number: 5395977
    Abstract: 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: Grant
    Filed: March 12, 1993
    Date of Patent: March 7, 1995
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Fumio Toda, Yorihiko Inoue, Masayoshi Minai
  • Patent number: 5288811
    Abstract: 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: Grant
    Filed: November 5, 1992
    Date of Patent: February 22, 1994
    Assignee: Exxon Research and Engineering Company
    Inventor: Stanley J. Brois
  • Patent number: 5288701
    Abstract: 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: Grant
    Filed: July 1, 1991
    Date of Patent: February 22, 1994
    Assignee: Givaudan-Roure Corporation
    Inventor: Josianne Baudin
  • Patent number: 5276199
    Abstract: 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: Grant
    Filed: February 11, 1993
    Date of Patent: January 4, 1994
    Assignee: Ethyl Corporation
    Inventors: John Y. Lee, Meng-Sheng Ao, Stephen E. Belmont
  • Patent number: 5180844
    Abstract: 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: Grant
    Filed: July 9, 1991
    Date of Patent: January 19, 1993
    Assignee: Daiso Co., Ltd.
    Inventors: Takashi Takahashi, Yoshikazu Takehira
  • Patent number: 5149711
    Abstract: 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: Grant
    Filed: March 7, 1989
    Date of Patent: September 22, 1992
    Assignee: Teijin Limited
    Inventors: Atsuo Hazato, Seizi Kurozumi
  • Patent number: 5149843
    Abstract: 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: Grant
    Filed: June 7, 1991
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5075478
    Abstract: 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: Grant
    Filed: January 17, 1991
    Date of Patent: December 24, 1991
    Assignee: G. D. Searle & Co.
    Inventors: James R. Behling, John R. Medich
  • Patent number: 4992577
    Abstract: 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: Grant
    Filed: May 22, 1989
    Date of Patent: February 12, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
  • Patent number: 4981872
    Abstract: 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: Grant
    Filed: January 15, 1988
    Date of Patent: January 1, 1991
    Assignee: Sankyo Company Limited
    Inventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Keiichi Tabata, Nobuyoshi Iwata
  • Patent number: 4942256
    Abstract: 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: Grant
    Filed: December 13, 1988
    Date of Patent: July 17, 1990
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 4921995
    Abstract: 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: Grant
    Filed: February 9, 1988
    Date of Patent: May 1, 1990
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi, Masahiro Koga
  • Patent number: 4904640
    Abstract: 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: Grant
    Filed: March 4, 1988
    Date of Patent: February 27, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Thomas Markert, Klaus Bruns, Horst-Juergen Krause, Josef Penninger, Michael Virnig, Volker Falk
  • Patent number: 4894483
    Abstract: 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: Grant
    Filed: October 28, 1987
    Date of Patent: January 16, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Hans-Dieter Martin, Roland Kramme, Ralf T. Weimann
  • Patent number: 4892966
    Abstract: 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: Grant
    Filed: July 16, 1987
    Date of Patent: January 9, 1990
    Assignee: Givaudan Corporation
    Inventor: Hans J. Wild
  • Patent number: 4847370
    Abstract: 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: Grant
    Filed: October 21, 1987
    Date of Patent: July 11, 1989
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Harry Finch, Duncan B. Judd, James D. Meadows
  • Patent number: 4756764
    Abstract: 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: Grant
    Filed: February 26, 1987
    Date of Patent: July 12, 1988
    Assignee: Firmenich SA
    Inventors: Alan F. Thomas, Alistair Y. Smith
  • Patent number: 4711895
    Abstract: 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: Grant
    Filed: October 22, 1985
    Date of Patent: December 8, 1987
    Assignee: Teijin Limited
    Inventors: Atsuo Hazato, Satsohi Sugiura, Seizi Kurozumi, Ryoji Noyori
  • Patent number: 4703127
    Abstract: 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: Grant
    Filed: September 2, 1983
    Date of Patent: October 27, 1987
    Assignee: The Australian National University
    Inventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
  • Patent number: 4696944
    Abstract: 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: Grant
    Filed: March 14, 1985
    Date of Patent: September 29, 1987
    Assignee: National Research Development Corporation
    Inventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay
  • Patent number: 4693845
    Abstract: 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: Grant
    Filed: June 18, 1986
    Date of Patent: September 15, 1987
    Assignee: KAO Corporation
    Inventors: Yoshiaki Fujikura, Akira Yamamuro, Motoki Nakajima
  • Patent number: 4668828
    Abstract: 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: Grant
    Filed: May 6, 1983
    Date of Patent: May 26, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: George L. Nelson
  • Patent number: 4663486
    Abstract: 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: Grant
    Filed: May 6, 1983
    Date of Patent: May 5, 1987
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: George L. Nelson
  • Patent number: 4661641
    Abstract: 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: Grant
    Filed: May 29, 1984
    Date of Patent: April 28, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
  • Patent number: 4625066
    Abstract: 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: Grant
    Filed: November 29, 1984
    Date of Patent: November 25, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Ludwig Elbe
  • Patent number: 4622410
    Abstract: 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: Grant
    Filed: March 18, 1985
    Date of Patent: November 11, 1986
    Assignee: Ono Pharmaceutical Co. Ltd.
    Inventors: Nobuyuki Hamanaka, Hideo Takada, Yoshinobu Arai
  • Patent number: 4618687
    Abstract: A cyclopentenone compound represented by the following formula: ##STR1## has an antitumor effect and can be produced from the antibiotic XK-213.
    Type: Grant
    Filed: April 18, 1985
    Date of Patent: October 21, 1986
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Tadashi Hirata, Hiromitsu Saito, Makoto Morimoto
  • Patent number: 4612308
    Abstract: 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: Grant
    Filed: November 29, 1984
    Date of Patent: September 16, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Gary A. Truitt, Milan R. Uskokovic, Peter M. Wovkulich
  • Patent number: 4576962
    Abstract: 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: Grant
    Filed: May 4, 1984
    Date of Patent: March 18, 1986
    Assignee: The Procter & Gamble Company
    Inventor: Randall S. Matthews
  • Patent number: 4571345
    Abstract: 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: Grant
    Filed: June 13, 1983
    Date of Patent: February 18, 1986
    Assignee: Cumberland Packing Corp.
    Inventors: Michael S. Verlander, William D. Fuller, Murray Goodman
  • Patent number: 4567004
    Abstract: 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: Grant
    Filed: July 18, 1984
    Date of Patent: January 28, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Erich Wolters
  • Patent number: 4543421
    Abstract: 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: Grant
    Filed: May 11, 1983
    Date of Patent: September 24, 1985
    Assignee: Miles Laboratories, Inc.
    Inventors: Paul F. Corey, Harold C. Kluender