Six-membered Alicyclic Ring Containing Patents (Class 568/376)
  • Patent number: 5919986
    Abstract: Compounds of formula I: ##STR1## wherein the dotted carbon-carbon bond in the D-ring is C--C or C.dbd.C; C(R,R) is CH.sub.2 or C.dbd.CH.sub.2,R.sup.1 is H, F or OH,R.sup.2 and R.sup.3 are each independently C.sub.1-4 -alkyl or CF.sub.3, or together with the carbon to which they are bound form C.sub.3-6 -cycloalkyl.are useful in the treatment of vitamin D dependent disorders, such as psoriasis, leukemia; acne and seborrhoic dermatitis; osteoporosis hyperparathyroidism accompanying renal failure; and multiple sclerosis.
    Type: Grant
    Filed: October 13, 1998
    Date of Patent: July 6, 1999
    Assignee: Hoffmann-la Roche Inc.
    Inventors: Pierre Barbier, Franz Bauer, Peter Mohr, Marc Muller, Wolfgang Pirson
  • Patent number: 5908944
    Abstract: This invention describes a new methylation or ethylation agent containing trimethyl aluminum or dimethyl zinc or triethyl aluminum as methyl or ethyl source, which additionally contains catalytic amounts of one or more copper(I) and/or copper(II) compounds as well as a process for the 1,4-addition of a methyl or ethyl group to an .alpha.,.beta.-unsaturated or an .alpha.,.beta.-double unsaturated ketone or an .alpha.,.beta.-unsaturated aldehyde using the agent according to the invention.By using only catalytic amounts of copper and a CKW (chlorinatedhydrocarbon)-free reaction medium, the new methylation/ethylation agent/process is distinguished by its environmental compatibility and it is, for example, suitable for the production of initial products for the synthesis of biologically effective compounds.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: June 1, 1999
    Assignee: Schering Aktiengesellschaft
    Inventors: Jurgen Westermann, Klaus Nickisch
  • Patent number: 5886233
    Abstract: Described are cyclohexanone derivatives of the formula (I), a method of preparing them and intermediates used in their preparation.
    Type: Grant
    Filed: August 8, 1997
    Date of Patent: March 23, 1999
    Assignee: Schering Aktiengesellschaft
    Inventors: Andreas Steinmeyer, Gunter Neef, Gunnar Muller, Hans-Joachim Knolker
  • Patent number: 5731283
    Abstract: Described are 1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different hydrogen or methyl; wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond; wherein the wavy line represents a carbon carbon single bond or a carbon carbon double bond; with the proviso that when the wavy line is a carbon carbon single bond then the dashed line is a carbon carbon single bond; wherein Y represents a moiety selected from the group consisting of: ##STR2## wherein H represents hydrogen, C.sub.1 -C.sub.4 lower alkyl or C.sub.1 -C.sub.2 acyl; and wherein R.sub.1 represents C.sub.1 -C.sub.4 lower alkyl with the additional proviso that when Y is the moiety: ##STR3## then the dashed line is a carbon carbon single bond, and uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, perfumed articles and colognes.
    Type: Grant
    Filed: January 28, 1997
    Date of Patent: March 24, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, James Joseph Koestler, Jan Van Elst
  • Patent number: 5728891
    Abstract: A process for the preparation of 3,3,5-trimethylcyclohexanone by catalytic hydrogenation of isophorone, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding isophorone and hydrogen to an upper part of a reactor to catalytically hydrogenate said isophorone to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein isophorone is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating step (c) until the subsequent reactor is the last reactor,(e) recovering the remainder of said subseque
    Type: Grant
    Filed: June 26, 1996
    Date of Patent: March 17, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Wilfried Bueschken, Juergen Hummel
  • 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: 5600007
    Abstract: The invention relates to the use of .alpha.-hydroxyketoalkyl derivatives as light protection filters for cosmetic or pharmaceutical products, the .alpha.-hydroxyketoalkyl group being linked, if appropriate via a spacer, to a chromophoric group which has an absorption maximum in a wavelength range of between 280 and 400 nm and has a conjugated .pi.-electron system of at least 8 .pi.-electrons, and to new .alpha.-hydroxyalkyl derivatives, processes for their preparation and pharmaceutical and cosmetic formulations comprising these derivatives as light protection substances.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: February 4, 1997
    Assignee: Merck Gmbh
    Inventors: Roland Martin, Ingeborg Stein, Ulrich Heywang, Michael Schwarz, Thekla Kurz
  • Patent number: 5597932
    Abstract: The invention is drawn to a compound having the following formula ##STR1## in which X.sup.1 and X.sup.2, which may be the same or different, represent hydrogen or a hydroxy-protecting group, X.sup.4 is hydrogen, A is selected from --COOAlkyl and CH.sub.2 OH, and B is a hydroxy group, or A and B, when taken together, represent an oxo group. These compounds are useful as intermediates in the production of 19-nor vitamin D derivatives.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: January 28, 1997
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
  • Patent number: 5510539
    Abstract: Liquid highly active photoinitiators are obtained by dissolving a solid photoinitiator of the titanocene type in liquid photoinitiators of the acetal or ketal type. The liquid mixtures have a long dark storage stability.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: April 23, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Godwin Berner, Franciszek Sitek, Rinaldo Husler
  • 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: 5466827
    Abstract: Thioalkane .alpha.,.beta.-diketones have interesting organoleptic properties and are therefore suitable as aroma substances.
    Type: Grant
    Filed: September 28, 1993
    Date of Patent: November 14, 1995
    Assignee: Haarmann & Reimer GmbH
    Inventors: Heinz-Jurgen Bertram, Roland Emberger, Matthias Guntert, Peter Werkhoff
  • Patent number: 5334740
    Abstract: Cyclohexanetriol derivatives represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are the same or different, and each denotes a hydrogen atom or a protecting group of a hydroxyl group,X denotes an oxygen atom, .dbd.CHCH.sub.2 OR.sup.4, .dbd.CHCHO or .dbd.CHCO.sub.2 R.sup.5, Y denotes a hydrogen atom and Z denotes --OR.sup.6, or Y and Z together form a single bond; or X and Z together form .dbd.NO--, .dbd.CHCH(OR.sup.7)O-- or .dbd.CHCO.sub.2 -- and Y is a hydrogen atom, R.sup.4 and R.sup.6 denote a hydrogen atom or a protecting group of a hydroxyl group respectively, R.sup.5 denotes a lower alkyl group, and R.sup.7 denotes a hydrogen atom or a lower alkyl group.Said derivatives are useful as synthetic intermediates of 1-hydroxyvitamin D derivatives.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: August 2, 1994
    Assignee: Kurary Co., Ltd.
    Inventors: Takashi Takahashi, Manzo Shiono
  • Patent number: 5326748
    Abstract: The invention relates to compounds of formula ##STR1## having a double bond in one of the positions indicated by the dotted lines. Compounds (I) are useful as perfuming ingredients for the preparation of perfuming compositions and perfuming articles, to which they impart sandalwood-animal notes.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: July 5, 1994
    Assignee: Firmenich SA
    Inventor: Christian Chapuis
  • Patent number: 5300654
    Abstract: .beta.-hydroxyketones are prepared by reacting an aldehyde with acetone in the presence of perhydroisoindole or pyrrolidine and water. The resulting .beta.-hydroxyketone is further reacted in the presence of a solvent mixture to produce .alpha.-.beta.-unsaturated ketones.
    Type: Grant
    Filed: July 15, 1991
    Date of Patent: April 5, 1994
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Masashi Nakajima, Tadashi Kyotani, Mikio Sawaki
  • 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: 5262552
    Abstract: An optically active (S)- or (R)-pentane compound of the general formula (11): ##STR1## wherein R.sub.11, R.sub.12 and R.sub.13 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R.sub.14 represents a hydroxy, protected hydroxy or oxo group, if R.sub.14 is an oxo group, the ring denoting benzene in the above formula (11) is benzoquinone, R.sub.15 represents a hydrogen atom, hydroxy or acyloxy group, R.sub.16 represents a hydroxy or acyloxy group, and the chiral central carbon marked with a symbol * in said formula (11) alternatively has one of an R-configuration and an S-configuration, is disclosed. Further, intermediate products of the compound of the formula (11) are also disclosed. Still further, a process for manufacturing the above compounds is disclosed. The compound of the formula (11) is easily synthesized from an easily available optically active starting material.
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: November 16, 1993
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5248831
    Abstract: Ethers of 1-hydroxy-hex-5-en-2-one are useful odoriferous substances which have a very complex fragrance pattern and allow an interesting variation in the scent of perfume oils.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: September 28, 1993
    Assignee: Haarmann & Reimer GmbH
    Inventors: Rudolf Hopp, Thomas Thielmann, Wilhelm Gottsch
  • Patent number: 5245041
    Abstract: A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.
    Type: Grant
    Filed: December 18, 1991
    Date of Patent: September 14, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • Patent number: 5228898
    Abstract: This invention relates to substituted bicycloheptadione derivatives with high herbicidal activity which are represented by general formula (I) ##STR1## (where R.sup.1 is a lower alkyl group, a phenyl group which may be substituted, an aralkyl group which may be substituted, or a heterocyclic group which may be substituted;R.sup.2 is, same or different, a halogen, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkyl group, an alkoxyalkyl group, or an alkoxylcarbonyl group, and n is 0 to 4;R.sup.3 and R.sup.4 are, same or different, hydrogen or a lower alkyl group).
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: July 20, 1993
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Akiyoshi Ueda, Shigemi Suga, Hiroyuki Adachi, Toshio Aihara, Kazuyuki Tomida, Hideki Yamagishi, Hideo Hosaka
  • Patent number: 5168983
    Abstract: A process for separating cyclohexanol and other impurities from a mixture containing cyclohexanone and cyclohexanol is disclosed.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: December 8, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Kazuo Tan, Kazuhiro Fujii, Michio Nakamura, Kazunao Hanada
  • Patent number: 5166448
    Abstract: A fluorine-substituted compound containing an ether bond and an intermediate thereof are described, which are represented by: ##STR1## wherein R represents a straight-chain alkyl group having 1 to 8 carbon atoms; n represents an integer of 2 to 7; m represents 1 or 2, X represents a hydrogen atom or a fluorine atom, and ##STR2## represents a trans-(equatorial-equatorial)cyclohexane ring. A compound represented by formula (II): ##STR3## wherein R represents a straight-chain alkyl group having 1 to 8 carbon atoms; n represents an integer of 2 to 7; m represents 1 or 2, ##STR4## represents a trans-(equatorial-equatorial)cyclohexane ring.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: November 24, 1992
    Assignee: Dainippon Ink & Chemicals, Inc.
    Inventors: Makoto Sasaki, Haruyoshi Takatsu, Kiyofumi Takeuchi
  • Patent number: 5164518
    Abstract: The present invention provides a method for the alpha,omega-arylation/alkylation of a non-conjugated diene in one step by reacting the diene with an aryl iodide or an aryl bromide and a carbon nucleophile in the presence of an amount of a Pd(O) complex effective to catalyze the reaction.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: November 17, 1992
    Assignee: Iowa State University Research Fondation Inc.
    Inventor: Richard C. Larock
  • 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: 5118856
    Abstract: A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: June 2, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • Patent number: 5118865
    Abstract: Novel compounds of formula ##STR1## wherein the dotted lines indicate the location of a single or double bond, symbol R.sup.1 stands for a hydrogen atom or a methyl radical, symbol R.sup.2 represents a linear or branched, saturated or unsaturated, C.sub.1 to C.sub.4 alkyl radical, provided that R.sup.1 is not hydrogen when R.sup.2 represents a methyl or n-propyl radical and the ring is saturated. Compounds (Ia) are useful as perfuming ingredients.A process for their preparation is disclosed.
    Type: Grant
    Filed: March 11, 1991
    Date of Patent: June 2, 1992
    Assignee: Firmenich SA
    Inventors: Christian Chapuis, Karl-Heinrich Schulte-Elte, Herve Pamingle, Christian Margot
  • Patent number: 5087612
    Abstract: A compound of formula ##STR1## wherein R.sup.1 represents a hydrogen atom or a saturated, linear or branched, alkyl radical, having from 1 to 4 carbon atoms, and R.sup.2 designates a lower alkyl radical, saturated or unsaturated, linear or branched;or any mixture containing a predominant amount of said compound (I), together with its isomer of formula ##STR2## wherein R.sup.1 and R.sup.2 are defined as above. Compounds (I) and their mixtures mentioned above develop odor notes of the woody-amber type and are therefore used as perfuming ingredients for the preparation of perfuming compositions and perfumed articles.A process for the preparation of compounds (I) and their mixtures is disclosed.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: February 11, 1992
    Assignee: Firmenich SA
    Inventor: Christian Chapuis
  • Patent number: 4994152
    Abstract: Small amounts of a medium-boiling fraction are removed from a liquid mixture by distillation using a distillation column (main column) having a rectifying part and a stripping part, the liquid mixture containing relatively large amounts of lower-boiling and higher-boiling components, and the rectifying part being connected to the upper end of a second distillation column (side column) and the stripping part to the lower end of the said column, and the medium-boiling fraction being removed in vapor or liquid form from its middle section, by a process in which the concentration of the medium-boiling fraction in the liquid mixture is less than 2%, preferably less than 0.1%, and the amount of vapor passed into the lower end of the side column from the main column is 1-20%, preferably 3-10%, based on the amount of vapor in the main column at the relevant point.
    Type: Grant
    Filed: December 27, 1989
    Date of Patent: February 19, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Kaibel, Karl Schloemer, Hans-Horst Mayer
  • 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: 4992563
    Abstract: This invention relates to several intermediates useful in preparing thromboxane A.sub.2 inhibiting (.+-.)7-[3.alpha.-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-1.alpha ., 4.alpha.-bicyclo[2.2.1]hept-2.beta.-yl]-heptenoic acids and useful derivatives thereof from (.+-.)octahydro-1.alpha.-methyl-3a.alpha., 7a.alpha.-4.alpha.,7.alpha.-methano-2H-inden-2-ones.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: February 12, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 4983723
    Abstract: A cycloalkane derivative represented by the formula (I): ##STR1## wherein A, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, Z, and n are as defined in the specification. The compounds of formula (I) exhibit activities against peptic ulcers and are useful as therapeutic and prophylactic agents for peptic ulcers.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: January 8, 1991
    Assignee: Green Cross Corporation
    Inventors: Hitoshi Yasuda, Chikara Fukaya, Kanemichi Okano, Kazumasa Yokoyama
  • Patent number: 4983584
    Abstract: A therapeutic and prophylactic agent for peptic ulcers comprising as an effective ingredient a cyclohexane derivative represented by general formula (I): ##STR1## wherein A represents a group shown by formula, >CH.sub.2, ##STR2## wherein X represents ethynylene, vinylene or ethylene, Y represents oxo or a hydroxy group; R.sup.1, R.sup.3, R.sup.4 and R.sup.5 each represents a hydrogen atom or alkyl; R.sup.2 represents a hydrogen atom, alkyl or a group shown by --OR.sup.8 ;R.sup.6 represents a hydrogen atom, oxo or a group shown by --OR.sup.8 ; and R.sup.7 represents a hydrogen atom or a group shown by --OR.sup.8, wherein R.sup.8 represents a hydrogen atom or an organic residue.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: January 8, 1991
    Assignee: Green Cross Corporation
    Inventors: Chikara Fukaya, Hitoshi Yasuda, Toshiaki Akira, Masakazu Iwai, Kanemichi Okano, Kazumasa Yokoyama
  • Patent number: 4960946
    Abstract: The present invention relates to novel substituted cyclohexanol compounds possessing a sandalwood aroma which are useful as fragrance materials. The invention also provides methods for synthesis thereof through a novel aldehyde intermediate. The compounds of the invention have the formula: ##STR1## wherein A is ##STR2## and wherein R.sub.1 is methyl or ethyl, R.sub.2 -R.sub.7 are independently hydrogen or methyl with the proviso that a maximum of two of the substituents R.sub.2 -R.sub.7 are methyl, and R.sub.8 is hydrogen, lower alkyl (C.sub.1 to C.sub.5) or acyl. The invention also provides fragrance compositions which utilize the compounds of the invention to impart a sandalwood aroma to perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: October 13, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF K&F
    Inventors: Robert Eilerman, Philip Christenson, John Yurecko, Jr., Thomas Zebovitz
  • Patent number: 4950797
    Abstract: A process for the preparation of carbonyl compounds by catalyzed isomerization of allyl alcohols in a tertiary phosphine or phosphite ester in the presence of a rhodium compound at a temperature of from 80.degree. C. to 180.degree. C., a carrier gas being passed through the reaction mixture and the carbonyl compound being separated from the emergent gas mixture by cooling.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Werner Bertleff, Michael Roeper
  • Patent number: 4936906
    Abstract: Agents for regulating plant growth containing an effective amount of at least one cyclohexanone derivative of the formula I ##STR1## where A, X, n, Y, Z and R have the meanings given in the disclosure, or salts of these compounds, and a process for regulating plant growth.
    Type: Grant
    Filed: July 2, 1986
    Date of Patent: June 26, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Jahn, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Rainer Becker, Johann Jung, Wilhelm Rademacher
  • Patent number: 4908479
    Abstract: A process for preparing a 2,2,6,6-tetrahalocyclohexanimine derivative (I) which comprises reacting a 2,2,6,6-tetrahalocyclohexanone with a primary amine or ammonia in the presence of a Lewis acid, a process for preparing a 2,6-dihaloaniline derivative (II) which comprises subjecting the 2,2,6,6-tetrahalocyclohexaneimine derivative (I) to dehydrohalogenation in the presence or absence of a catalyst, and an N-phenyl-2,2,6,6-tetrahalocyclohexaneimine. According to the process of the present invention, the 2,2,6,6-tetrahalocyclohexaneimine derivative (I) can be prepared from inexpensive starting materials in high yield through a few steps. Also, the 2,6-dihaloaniline derivative (II) can be prepared from inexpensive starting materials in high yield and high purity through a few steps. Further, the N-phenyl-2,2,6,6-tetrahalocyclohexaneimine is very useful in the preparation of N-phenyl-2,6-dihaloaniline.
    Type: Grant
    Filed: August 3, 1988
    Date of Patent: March 13, 1990
    Assignee: Osaka Yuki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Takeaki Saeki, Hideo Ishikawa, Tunehei Oki
  • Patent number: 4898986
    Abstract: Disclosed is a novel inosose compound represented by the general formula: ##STR1## wherein X.sup.1 and X.sup.2 are both halogen; X.sup.1 is hydrogen and X.sup.2 is halogen; or X.sup.1 is --SQ.sup.1 and X.sup.2 is --SQ.sup.2 (each of Q.sup.1 and Q.sup.2 is lower alkyl or Q.sup.1 and Q.sup.2 may form lower alkylene), R.sup.1 is a protective group for hydroxyl and Y is .dbd.O, .dbd.N--Z (Z is hydroxyl which may be protected) or ##STR2## (A is hydrogen or an amine residue), particularly to the compound wherein the symbol Y is oxygen.The inosose compound is useful as intermediates for production of valiolamine and the N-substituted derivatives thereof, which have potent .alpha.-glucosidase inhibiting activities and are useful as preventives or therapeutics for symptoms of hyperglycemia and various diseases derived therefrom in human and animals, such as diabetes, obesity and hyperlipemia.
    Type: Grant
    Filed: August 31, 1987
    Date of Patent: February 6, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Satoshi Horii, Hiroshi Fukase
  • 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: 4886891
    Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
  • Patent number: 4868339
    Abstract: Multimethyl cyclohexene or cyclohexane derivatives having woody, spicy, amber or violet odors are disclosed. The derivatives can be formulated into perfurmes, talcs, lotions, cremes and air fresheners.
    Type: Grant
    Filed: September 23, 1987
    Date of Patent: September 19, 1989
    Assignee: BASF K & F Corporation
    Inventors: Philip A. Christenson, Brian J. Drake
  • Patent number: 4855460
    Abstract: A process for the preparation of perfluoroalkylated ketones and/or perfluoroalkylated alcohols, comprising the step of contacting a perfluoroalkyl iodide or perfluoroalkyl bromide with an acid anhydride, in the presence of a metal chosen from zinc and cadmium.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: August 8, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Tordeux, Claude Wakselman, Catherine Francese
  • Patent number: 4838932
    Abstract: A method of controlling undesirable vegetation utilizing an herbicidal compounds of the formula ##STR1## wherein X NR.sup.9 wherein R.sup.9 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl, with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;R.sup.7 and R.sup.
    Type: Grant
    Filed: August 20, 1987
    Date of Patent: June 13, 1989
    Assignee: Stauffer Chemical Company
    Inventor: Christopher G. Knudsen
  • Patent number: 4827004
    Abstract: Novel Isoprene Derivatives which have mucosa-protective and gastric acid secretion-inhibiting properties and are useful for combatting ulcers both by treating and as a prophylaxis against gastric and/or duodenal ulcers.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: May 2, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
  • Patent number: 4820331
    Abstract: Cyclohexenone derivatives of the general formula ##STR1## where R is C.sub.1 -C.sub.6 -alkyl, cyclopropyl, phenyl or C.sub.2 -C.sub.6 -alkoxyalkyl, R.sup.1 is hydrogen, tetrahydropyran-2-yl, benzoyl or unsubstituted or halo-substituted C.sub.1 -C.sub.6 -alkanoyl, and R.sup.2 is hydrogen or C.sub.1 -C.sub.6 -alkyl, and phytophysiologically tolerable salts thereof, and their use for regulating plant growth.
    Type: Grant
    Filed: December 3, 1987
    Date of Patent: April 11, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Keil, Ulrich Schirmer, Dieter Kolassa, Juergen Kast, Wilhelm Rademacher, Johann Jung
  • Patent number: 4792618
    Abstract: Fluoro-substituted carbocyclic compounds are prepared by(A) reacting hydrogen fluoride with a chloro-cyclohexenyl compound of the formula ##STR1## where R.sub.1 and R.sub.2 are independently selected from the group consisting of --H, --CH.sub.2 OH, --COF, --COCl, --CF.sub.3, --CN, ##STR2## and --CH.sub.2 R, where R is --H or alkyl of 1-4 carbon atoms, to form a gem-dihalocyclohexane compound of the formula ##STR3## where X is chlorine and R.sub.1 and R.sub.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: December 20, 1988
    Assignee: Occidental Chemical Corporation
    Inventors: Joseph F. Bieron, David Y. Tang
  • Patent number: 4788337
    Abstract: Described are 2-alkanoyl-2-(1-penten-1-yl) cyclohexanones of my invention defined according to the structure: ##STR1## wherein R represents methyl or ethyl; a process for preparing same and organoleptic uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions and fabric softener articles. Also described are intermediates useful in carrying out the process for producing such 2-alkanoyl-2-(1-penten-1-yl) cyclohexanones of my invention defined according to the structure: ##STR2## wherein R represents methyl or ethyl.
    Type: Grant
    Filed: January 28, 1988
    Date of Patent: November 29, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Mark A. Sprecker
  • Patent number: 4760050
    Abstract: 1-Isopropyl-3-methyl-2-(but-2'-enoyl)cyclohexane derivatives having the general formula ##STR1## in which the dotted lines represent no double bond, one double bond at position 4 or two double bonds at positions 1 and 5, 2 and 4 or 4 and 6 are valuable fragrances with fruity flowery and green odors, in some cases accompanied by woody and/or herbal notes. Above defined compounds can be used as a perfume component in perfume compositions or in products to be perfumed.
    Type: Grant
    Filed: January 9, 1987
    Date of Patent: July 26, 1988
    Assignee: Naarden Intl. N.V.
    Inventors: Antonius J. A. Van Der Weerdt, Nicolaas L. J. Broekhof, Jan G. Witteveen
  • Patent number: 4749797
    Abstract: New tetra-alkyl-2,2,5,5-cyclohexanone-4-ol-1-compounds and their sulphonyl derivatives with the general formula: ##STR1## in which: each of R and R', identical or different, represents an alkyl radical (1-5 carbons) and R" represents a hydrogen atom or a radical SO.sub.2 R"' in which R"' represents an alkyl radical (1-5 carbons) or an aryl radical (6-14 carbons), the process and the intermediates for their preparation, as well as their use in the synthesis of cyclopropane lactones of cis structure.
    Type: Grant
    Filed: June 24, 1986
    Date of Patent: June 7, 1988
    Assignee: Roussel Uclaf
    Inventors: Jean D'Angelo, Gilbert Revial, Robert Azerad, Didier Buisson
  • Patent number: 4744820
    Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1 is --CHO or --CH(OR.sup.3).sub.2, R.sup.2 is alkyl or alkoxyalkyl, each of 1 to 4 carbon atoms, or cyclopropyl, and R.sup.3 is alkyl of 1 to 8 carbon atoms, and salts thereof, processes for their manufacture, and their use as agents for regulating plant growth.
    Type: Grant
    Filed: February 13, 1987
    Date of Patent: May 17, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Keil, Ulrich Schirmer, Dieter Kolassa, Wilhelm Rademacher, Johann Jung
  • Patent number: 4720591
    Abstract: Chloro-olefins which contain a group of the formula ##STR1## where Y is chlorine or hydrogen, which are prepared by a process in which a trichloromethyl compound which contains a group of the general formula ##STR2## where X is hydrogen or an organic radical, is reduced with a chromium(II) salt in an aqueous medium.
    Type: Grant
    Filed: December 12, 1986
    Date of Patent: January 19, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Steckhan, Reinhard Wolf, Hermann Puetter
  • 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