The -c(=x)x- Group Is In A Substituent Attached To The Ring Nitrogen Of The Five-membered Hetero Ring (e.g., Beta-pyrrolidyl Ethyl Ester Of Benzoic Acid, Etc.) Patents (Class 548/573)
  • Patent number: 4902818
    Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## in which R.sup.2 and R.sup.3 represents lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring, by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen, is described.The compounds of formula I are potential intermediates in the manufacture of, interalia, natural vitamin E and natural vitamin K.sub.1.
    Type: Grant
    Filed: October 5, 1988
    Date of Patent: February 20, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
  • Patent number: 4902334
    Abstract: A plant metabolism regulating agent comprising as an active ingredient an alpha,beta or beta,gamma-un-saturated carboxylic acid or its derivative. It is useful for controlling the metabolism of a plant, facilitating the growth of a beneficial plant such as cereals by inhibiting the growth of undesirable plants or eradicating them, regulating the growth of a plant and dwarfing a plant.
    Type: Grant
    Filed: October 31, 1984
    Date of Patent: February 20, 1990
    Assignee: Teijin Limited
    Inventors: Shizuo Azuma, Toshiyuki Hiramatsu, Teizo Yamaji, Yataro Ichikawa
  • Patent number: 4898977
    Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4880800
    Abstract: Compounds are described of the formula ##STR1## where: R.sup.1 is --H or --CH.sub.3,n is 1, m is 2-4 and X is --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 --;Y is a saturated heterocyclic amino group,R.sup.2 is (i) substituted or unsubstituted phenylalkyl, thineylalkyl or naphthylalkyl or (ii) cinnamyl, and their salts and solvates.These compounds inhibit blood platelet aggregation, bronchoconstriction and vasoconstriction and may be formualted for use as antithrombotic or antiasthmatic agents.
    Type: Grant
    Filed: September 15, 1987
    Date of Patent: November 14, 1989
    Assignee: Glaxo Group Limited
    Inventors: Christopher J. Wallis, Harry Finch, Peter Hallett
  • Patent number: 4833247
    Abstract: A process for the production of 2-benzyl fatty acids and esters thereof corresponding to the following formula ##STR1## comprising reacting 2-fatty alkyl-4,4-dimethyl-2-oxazolines with benzaldehydes corresponding to the formula R.sup.2 --C.sub.6 H.sub.4 --CHO to form 2-(1-benzylidene)-fatty alkyl-4,4-dimethyl-2-oxazolines, catalytically hydrogenating the products of this reaction to the 2-(1-benzyl)-fatty alkyl-4,4-dimethyl oxazolines and converting the products thus formed by acid-catalyzed hydrolysis or solvolysis with an alcohol of the formula R.sup.5 OH into the 2-benzyl fatty acids or esters thereof. Amidosulfonic acid gives particularly high yields as catalyst for the reaction of the 2-fatty alkyl-4,4-dimethyl-2-oxazolines with the benzaldehydes.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: May 23, 1989
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventor: Horst-Juergen Krause
  • Patent number: 4783537
    Abstract: Novel .alpha.-aryl-.alpha.-(.omega.-aminoalkyl)-.alpha.-[hydroxy(aralkyl and cycloalkyl)]acetic acid derivatives and .alpha.-aryl-.alpha.-(.omega.-aminoalkyl)-.alpha.[alkanoyloxy(aralkyl and cycloalkyl)]acetic acid derivatives, such as N,N-dimethyl-2-(hydroxyphenylmethyl)-4-dimethylamino-2-phenylbutanamide, 2-(hydroxyphenylmethyl)-5-dimethylamino-2-phenylpentanenitrile, ethyl 2-(hydroxyphenylmethyl)-5-dimethylamino-2-phenylpentanoate, and N,N-dimethyl-2[(acetyloxy)phenylmethyl]-4-dimethylamino-2-phenylbutanamide , useful in the treatment of cardiovascular disease.
    Type: Grant
    Filed: November 13, 1985
    Date of Patent: November 8, 1988
    Assignee: Pennwalt Corporation
    Inventor: Robert J. Murray
  • Patent number: 4766119
    Abstract: p is an integer from one to three;NR is selected from the group consisting of pyrrolidino, piperidino, morpholino and dialkylamino containing a total of two to eight carbon atoms either straight chain or branched; or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: February 20, 1985
    Date of Patent: August 23, 1988
    Assignee: United Pharmaceuticals, Inc.
    Inventor: William M. Davis
  • Patent number: 4760146
    Abstract: Novel compounds and processes for making and using them. The compounds include ethyl 1-[3-(1-piperidinyl)propyl]-6-phenyl-3-cyclohexene-1-carboxylate, 1-[3-(1-piperidinyl)propyl]-6-phenyl-3-cyclohexene-1-carboxyamide, and N,N-dimethyl-1-[3-(1-piperidinyl)propyl]-6-phenyl-3-cyclohexene-1-carboxam ide.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: July 26, 1988
    Assignee: Pennwalt Corporation
    Inventor: Bruce H. Toder
  • Patent number: 4736064
    Abstract: Prodrugs of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formula (I): ##STR1## and pharmaceutically acceptable salts thereof are disclosed.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: April 5, 1988
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Wasyl Halczenko, George Hartman
  • Patent number: 4727184
    Abstract: A composition comprising an aromatic copolyester-carbonate having flexural modulus, flexural yield and secondary transition temperature improvement over a corresponding aromatic polycarbonate effective amount of ester units of the structure ##STR1## or mixtures of the above two structures wherein R.sub.1 and R.sub.2 are the same or different and are alkyl of one to six carbon atoms, inclusive, cycloalkyl of four to seven carbon atoms, inclusive, phenyl, one to three alkyl substituted phenyl each alkyl having one to three carbon atoms, inclusive, and R.sub.1 and R.sub.2 taken together with the nitrogen to which they are attached form a ring of four to six carbon atoms, inclusive, or carbazole.
    Type: Grant
    Filed: October 20, 1986
    Date of Patent: February 23, 1988
    Assignee: General Electric Company
    Inventor: Niles R. Rosenquist
  • Patent number: 4721783
    Abstract: A new class of anti-spasmodic thioester compounds having a heterocyclic ring containing the nitrogen atom of a secondary or tertiary amine or a bicycloheterocyclic ring system containing the nitrogen atom of a secondary or tertiary amine. These compounds have the general formula I ##STR1## wherein: n is an integer from 0 to 2;R.sub.1 is aryl or cycloalkyl;R.sub.2 is hydrogen or hydroxyl; andR.sub.
    Type: Grant
    Filed: January 9, 1986
    Date of Patent: January 26, 1988
    Assignee: United Pharmaceuticals, Inc.
    Inventor: William M. Davis
  • Patent number: 4696941
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and represent a straight-chain or branched alkyl group of 1 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, a 2-furyl, 3-furyl, 3-pyridyl, 4-pyridyl or 2-thienyl group or an aromatic group of the formula ##STR2## wherein X, Y and Z are the same or different and represent hydrogen, alkyl of 1 to 3 carbon atoms, trifluoromethyl, alkoxy with 1 to 4 carbon atoms, halogen, nitro or hydroxy groups are useful as pharmaceutical, veterinary and cosmetic agents.
    Type: Grant
    Filed: June 28, 1985
    Date of Patent: September 29, 1987
    Assignee: Groupement d'Interet Economique dit: Centre International 'de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan
  • Patent number: 4686309
    Abstract: The invention provides compounds of formula: ##STR1## in which R=H, halogen, alkyl, alkyloxy, alkythio, NH.sub.2, alkylamino, dialkylamino or CF.sub.3, R.sub.3 =H or alkyl, either R.sub.4 and R.sub.5 =H and R.sub.1 and R.sub.2 =H or alkyl, optionally substituted by alkenyl (2 to 4 C) or alternatively R.sub.1 and R.sub.2 form together a saturated heterocyclic ring containing 4 to 7 ring members and optionally containing another heteroatom such as O, S or N optionally substituted by alkyl, or R.sub.4 =H, R.sub.1 =H or alkyl and R.sub.2 and R.sub.5 together form an alkylene (3 to 4 C) radical and (i) either A=alkyl or phenyl which is unsubstituted or substituted by one or two substituents chosen from halogen, alkyl, alkyloxy, alkylthio, NH.sub.2, alkylamino, dialkylamino, NO.sub.2 or CF.sub.3 or alternatively A=pyridyl, benzyl or cycloalkyl (3 to 6C), Y=S, SO or SO.sub.2 or a radical: ##STR2## in which R.sub.6 =H or alkyl and R.sub.
    Type: Grant
    Filed: February 15, 1985
    Date of Patent: August 11, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
  • Patent number: 4647562
    Abstract: A new class of anti-spasmodic compounds having three branch chains is provided. These compounds have the general formula: ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are saturated straight chain or branched alkyl groups contained from 1 to 8 carbon atoms, and are separated or linked to one another to form an aliphatic ring system. k is an integer from 0 to 5, and the total number of carbon atoms in R.sub.1 plus R.sub.2 plus R.sub.3 plus k are equal to or less than 12. Furthermore, l is an integer from 1 to 3, m is an integer from 1 to 3, n is an integer from 1 to 3, and X may be nonexistent or may be O, S, NH or CH.sub.2 or salts thereof. However, when X is nonexistent the terminal group in both the m chain and the n chain is a methyl group.
    Type: Grant
    Filed: February 20, 1985
    Date of Patent: March 3, 1987
    Assignee: United Pharmaceuticals, Inc.
    Inventor: William M. Davis
  • Patent number: 4621149
    Abstract: A process for producing a urethane compound which comprises reacting at least one compound selected from the group consisting of a primary amine, a secondary amine and a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of a catalyst system comprising:(a) at least one member selected from the group consisting of platinum group metals and compounds containing at least one platinum group element; and(b) at least one halogen-containing compound selected from the group consisting of alkali or alkaline earth metal halides, onium halides, compounds capable of forming onium halides in the reaction, oxo acids of halogen atoms and their salts, complex compounds containing halogen ions, organic halides and halogen molecules,in the presence of molecular oxygen and/or an organic nitro compound as an oxidizing agent at a temperature of from about 80.degree. C. to about 300.degree. C. under a pressure of from about 1 Kg/cm.sup.2 to about 500 Kg/cm.sup.2.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: November 4, 1986
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shinsuke Fukuoka, Masazumi Chono
  • Patent number: 4533732
    Abstract: This invention relates to derivatives of 3-propionylsalicylic acid represented by the formula (1) ##STR1## wherein R represents a hydrogen atom, a lower alkyl group or a group ##STR2## (wherein R.sup.1 and R.sup.2 represent a lower alkyl group or R.sup.1 and R.sup.2, when taken together with the nitrogen atom to which they are attached, may form a heterocyclic ring with or without an intervening hetero atom, and n is an integer of 1 to 4), and X represents a hydrogen atom or a halogen atom, R being the group ##STR3## when X is a hydrogen atom. This invention also relates to processes for preparing the same.
    Type: Grant
    Filed: September 30, 1983
    Date of Patent: August 6, 1985
    Assignees: Yamamoto Chemical Industrial Company, Limited, Osaka Municipal Government
    Inventors: Hiroshige Inoue, Kenichi Fukushima, Ikuzo Nishiguchi
  • Patent number: 4482549
    Abstract: Compounds are described of the formula ##STR1## in which --COR.sup.1 is a complex ester or thioester group,W is alkylene,X is cis or trans --CH.dbd.CH or --CH.sub.2 CH.sub.2 --,n is 1 or 2,Y is a saturated heterocyclic amino group having 5-8 ring members, andR.sup.2 is unsubstituted or substituted phenylalkyl, thienzlalkyl, naphthylalkyl or cinnamyl, and their salts and solvates.These compounds inhibit blood platelet aggregation and bronchoconstriction and may be formulated for use as antithrombotic and antiasthmatic agents.
    Type: Grant
    Filed: February 8, 1984
    Date of Patent: November 13, 1984
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, Norman F. Hayes, John Bradshaw, Malcolm Carter, Alan Wadsworth
  • Patent number: 4464490
    Abstract: Amino and amido dialkyltin dicarboxylates and stannoxy carboxylates are prepared by first reacting an amine or amino alcohol with a dicarboxylic acid anhydride, followed by reaction of the resulting product with a dialkyltin oxide. The obtained compounds are useful as catalysts for promoting reaction of organic isocyanates with organic compounds having one or more active hydrogen-containing groups.
    Type: Grant
    Filed: March 18, 1983
    Date of Patent: August 7, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Ibrahim S. Bechara, Rocco L. Mascioli
  • Patent number: 4455437
    Abstract: Herbicidally effective aminoalkyl esters of 2-nitro-5-(o-chloro-p-trifluoromethylphenoxy)-benzoic acid, and acid addition salts and quaternary ammonium salts thereof, are suitable for the selective control of weeds in crops of useful plants, for example soya bean and rice crops.The aminoalkyl esters correspond to the formula ##STR1## wherein A is a C.sub.2 -C.sub.4 -alkylene bridge or the direct bond, and ##STR2## is an open amino group, and ##STR3## is a cyclic amino group.
    Type: Grant
    Filed: December 28, 1979
    Date of Patent: June 19, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Durr, Otto Rohr, Beat Bohner
  • Patent number: 4447428
    Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH--or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: May 8, 1984
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Harry Finch, Roger F. Newton
  • Patent number: 4438112
    Abstract: Prostanoids are described of the formulae ##STR1## (and the salts thereof) in which: X is cis or trans --CH.dbd.CH-- or CH.sub.2 CH.sub.2 --;R.sup.1 is C.sub.1-7 alkyl terminated by --COOR.sup.10 where R.sup.10 is H, C.sub.1-6 alkyl or aralkyl;Y is a saturated heterocyclic amino group; andR.sup.4 is aralkyl (in which the aryl portion is substituted by alkylthio, alkylsulphinyl, alkylsulphonyl, alkanoylamino, aroylamino, phenalkyl, aminosulphonyl, alkanoylaminosulphonyl, phenylsulphonyl, nitro, tetrazolyl, substituted phenyl or thienyl).These compounds inhibit blood platelet aggregation and have bronchodilatory action, and may be formulated for use as anti-asthmatics and antithrombotic agents.
    Type: Grant
    Filed: September 17, 1982
    Date of Patent: March 20, 1984
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw
  • Patent number: 4432985
    Abstract: Described are compounds of the formula ##STR1## wherein R is hydrogen or loweralkyl; R.sub.1 is --OR.sub.2 or --NR.sub.2 R.sub.3 wherein R.sub.2 and R.sub.3 independently of one another denote hydrogen or loweralkyl; n is 0 or 1; R.sub.4 and R.sub.5 independently of one another denote loweralkyl or together form a 5 or 6 membered cycloalkyl substituted by hydrogen or loweralkyl, and together with the nitrogen atom, form a ring; and pharmaceutically acceptable salts thereof and their use as anticonvulsant agents in a method of controlling convulsions or seizures.
    Type: Grant
    Filed: March 15, 1982
    Date of Patent: February 21, 1984
    Assignee: Abbott Laboratories
    Inventors: Alex M. Nadzan, George R. Granneman
  • Patent number: 4430456
    Abstract: Amino and amido dialkyltin dicarboxylates and stannoxy carboxylates are prepared by first reacting an amine or amino alcohol with a dicarboxylic acid anhydride, followed by reaction of the resulting product with a dialkyltin oxide. The obtained compounds are useful as catalysts for promoting reaction of organic isocyanates with organic compounds having one or more active hydrogen-containing groups.
    Type: Grant
    Filed: September 16, 1982
    Date of Patent: February 7, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Ibrahim S. Bechara, Rocco L. Mascioli
  • Patent number: 4421927
    Abstract: The present invention relates to a new cinnamoyl-cinnamic acid derivative selected from the group constituted by:(i) the m-cinnamoyl-cinnamic acid derivatives of formula ##STR1## in which: X.sub.o,X.sub.1,X.sub.2,X.sub.3,X.sub.4, which are identical or different, each represent an atom of hydrogen, a halogen, a lower alkyl group, a lower alkoxy group, the group NRR' (where R and R' identical or different, each represent an atom of hydrogen or a lower alkyl group), the group NO.sub.2, CF.sub.3 or OH;R.sub.1 represents an atom of hydrogen or a lower alkyl group;R.sub.2 represents an atom of hydrogen or the methyl group;Y represents a group OH, OR.sub.3 (where R.sub.3 is a lower alkyl group), NRR' (where R and R' are defined as hereinabove) or the group O(CH.sub.2).sub.n NR.sub.4 R.sub.5 (where n is an integer of value 1 to 5--and preferably 2 or 3)--; and R.sub.4 and R.sub.
    Type: Grant
    Filed: October 22, 1981
    Date of Patent: December 20, 1983
    Assignee: Societe de Recherches Industrielles (S.O.R.I.)
    Inventor: Francois Picart
  • Patent number: 4410521
    Abstract: Compounds are described of the formula ##STR1## in which --COR.sup.1 is a complex ester or thioester group,W is alkylene,X is cis or trans --CH.dbd.CH or --CH.sub.2 CH.sub.2 --,n is 1 or 2,Y is a saturated heterocyclic amino group having 5-8 ring members, andR.sup.2 is unsubstituted or substituted phenylalkyl, thienylalkyl, naphthylalkyl or cinnamyl,and their salts and solvates.These compounds inhibit blood platelet aggregation and bronchoconstruction and may be formulated for use as antithrombotic and antiasthmatic agents.
    Type: Grant
    Filed: September 16, 1982
    Date of Patent: October 18, 1983
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, Norman F. Hayes, John Bradshaw, Malcolm Carter
  • Patent number: 4409213
    Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.
    Type: Grant
    Filed: November 10, 1982
    Date of Patent: October 11, 1983
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Harry Finch, Roger F. Newton, Christopher J. Wallis
  • Patent number: 4391827
    Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.
    Type: Grant
    Filed: July 27, 1981
    Date of Patent: July 5, 1983
    Assignee: Pfizer Inc.
    Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4360670
    Abstract: Amino and amido dialkyltin dicarboxylates and stannoxy carboxylates are prepared by first reacting an amine or amino alcohol with a dicarboxylic acid anhydride, followed by reaction of the resulting product with a dialkyltin oxide. The obtained compounds are useful as catalysts for promoting reaction of organic isocyanates with organic compounds having one or more active hydrogen-containing groups.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: November 23, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Ibrahim S. Bechara, Rocco L. Mascioli
  • Patent number: 4356313
    Abstract: The invention relates to novel [(5,6,9a-substituted-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]alkanoi c and cycloalkanoic acids and their analogs, esters, salts and derivatives. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful in the treatment and prevention of injury to the brain and spinal chord due to accidents, ischemic stroke and hydrocephalus; compositions for such uses are also disclosed.
    Type: Grant
    Filed: February 19, 1981
    Date of Patent: October 26, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Gerald E. Stokker, Norman P. Gould
  • Patent number: 4356314
    Abstract: The invention relates to novel [(5,6,9a-substituted-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]alkanoi c and cycloalkanoic acids, and their analogs, esters, salts and derivatives. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful in the treatment and prevention of injury to the brain and spinal chord due to accidents, ischemic stroke and hydrocephalus; compositions for such uses are also disclosed.
    Type: Grant
    Filed: February 19, 1981
    Date of Patent: October 26, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Gerald E. Stokker, Norman P. Gould
  • Patent number: 4332941
    Abstract: Cyclohexanones and -hexenones ##STR1## R.sup.1 is hydrogen or--CO--O--C.sub.n H.sub.2n+1-m (--NR.sup.4 R.sup.5) (1c)R.sup.2 is a group 1c, R.sup.3 is C.sub.1 - to C.sub.10 -alkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, trifluoromethyl, nitro, cyano, chloro, carbamoyl, lower-alkyl-carbamoyl, sulfamoyl or lower-alkyl-sulfamoyl, R.sup.4 and R.sup.5 are lower alkyl or --NR.sup.4 R.sup.5 is pyrrolidinyl, piperidyl or morpholyl, m is 1 or 2 and n is 2 to 6, are obtained by reacting 2 mols of an esterCH.sub.3 --CO--CH.sub.2 --CO--O--C.sub.n H.sub.2n+1-m (--NR.sup.4 R.sup.5).sub.m (2)with an aldehyde R.sup.3 --CHO (3). The compounds (1) easily saponify and decarboxylate without an added catalyst to form a cyclohexenones ##STR2## while setting free the alcoholHO--C.sub.n H.sub.2n+1-m (--NR.sup.4 R.sup.5).sub.m (5)which reacts without a catalyst with diketene to form the ester (2).
    Type: Grant
    Filed: October 10, 1980
    Date of Patent: June 1, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudiger Berthold, Werner H. Muller