Bicyclo Ring System Having The Spiro Hetero Ring As One Of The Cyclos (e.g., Griseofulvin, Etc.) Patents (Class 549/345)
  • Patent number: 5071871
    Abstract: New benz[b]pyranes and pyranopyridines of formula I, ##STR1## wherein the significances of substituents V, T, W, R.sub.3 to R.sub.5, R.sub.9, R.sub.10, m, X, Y and Z are given in claim 1 and their N-oxides and their salts and their use in the treatment of raised blood pressure in the treatment of vascular disorders and other disorders in which a reduction in tension of the smooth muscles is therapeutically useful, as well as in the treatment of hair loss and baldness. Further the compounds are useful in the treatment of asthma and obstructive disorders of the respiratory system as well as in the prophylactic treatment of obstructive or inflammatory airways disease, for example asthma, as well as novel pharmaceutical compositions comprising said K.sup.+ channel activators suitable for such use.
    Type: Grant
    Filed: July 10, 1990
    Date of Patent: December 10, 1991
    Assignee: Sandoz Ltd.
    Inventors: Stefan Blarer, John Morley, Ian D. Chapman
  • Patent number: 5066816
    Abstract: The present invention provides an industrially valuable method for preparing an optically active 3,4-dihydro-3,4-epoxy-2H-1-benzopyran compound which is useful as a starting material for an optically active benzopyran compound with antihypertensive, coronary blood flow-increasing activities and the like, and also provides a diastereomeric ester compound with a 3-halo-4-hydroxy-2H-1-benzopyran compound which is useful as an intermediate for said epoxy compound.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: November 19, 1991
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Shinro Setoguchi, Mineo Tsuruda, Chiaki Kitami, Tsutomu Yamanaka
  • Patent number: 5061813
    Abstract: Novel compounds are disclosed having the formula ##STR1## and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are as defined herein. These compounds are useful, for example, as cardiovascular agents and especially as anti-ischemic agents.
    Type: Grant
    Filed: April 2, 1990
    Date of Patent: October 29, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Karnail Atwal
  • Patent number: 5039672
    Abstract: Certain spirocyclic heterocyclic compounds, and their pharmaceutically-acceptable salts, are inhibitors of the aldose reductase enzyme, and so are useful for the control of diabetic complications. Exemplary compounds include compounds of the formula ##STR1## wherein Y is ##STR2## X is --O-- or ##STR3## R.sub.1 and R.sub.2 are each independently H, alkyl C.sub.1 -C.sub.6,aryl or arylalkyl (C.sub.1 -C.sub.6);W.sub.1 and W.sub.2 are each independently hydrogen, halogen or nitro; andthe pharmaceutically acceptable base addition salts thereof.
    Type: Grant
    Filed: April 5, 1990
    Date of Patent: August 13, 1991
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Eric R. Larson
  • Patent number: 5028711
    Abstract: Benzopyran derivatives of the general formula I ##STR1## are disclosed. The compounds are therapeutic active compounds.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: July 2, 1991
    Assignee: Beiersdorf Aktiengesellschaft
    Inventors: Wolfgang Stenzel, Theo Schotten, Ben Armah
  • Patent number: 5023352
    Abstract: Described are alkyl-substituted tetra- or hexahydrobenzopyran derivatives defined according to one of the generic structures: ##STR1## wherein Z is a moiety in the alternative either ##STR2## wherein in the moiety having the structure: ##STR3## R' is methyl or ethyl and in the moiety having the structure: ##STR4## one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds; wherein R.sub.1 and R.sub.2 taken separately represent hydrogen or C.sub.1 -C.sub.3 lower alkyl (with the proviso that R.sub.1 and R.sub.2 are not both hydrogen) or R.sub.1 and R.sub.2 taken together complete a C.sub.5 or C.sub.6 cycloalkyl moiety; and 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, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powder and perfumed polymers.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: June 11, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Marie R. Hanna, Charles E. J. Beck, Salvatore M. Brucato
  • Patent number: 5011845
    Abstract: Compounds of the formula ##STR1## wherein R.sup.5 represents C.sub.1 to C.sub.6 -alkyl or the group--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --Ar wherein Z represents O, S or --CH.sub.2 --and Ar is phenyl, optionally substituted by one or two groups selected from the group consisting of hydrogen, C.sub.1 to C.sub.6 -alkyl, C.sub.1 to C.sub.6 -alkoxy, Cl,F,Br,I,NO.sub.2, CF.sub.3, CN, R.sup.6 -S(O).sub.x, R.sup.7 --CO--,(R.sup.8 R.sup.9)NCO-and phenyl, wherein x is 0, 1 or 2, and each R.sup.6, R.sup.7, R.sup.8 and R.sup.9 is independently C.sub.1 to C.sub.6 alkyl or two adjacent groups on Ar may form together an additional fused benzenoid ring; n and m independently represent integers of from 1 to 8; and ring Q represents one of the rings Q.sub.1, Q.sub.2, Q.sub.3 or Q.sub.4 below: ##STR2## X is N or C--R.sup.1 ; Y is N or C--R.sup.4 ;W represents O or S;each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is independently selected from hydrogen, C.sub.1 to C.sub.6 -alkyl, C.sub.1 to C.sub.6 -alkoxy, Cl,F,Br,I,NO.sub.
    Type: Grant
    Filed: June 13, 1990
    Date of Patent: April 30, 1991
    Assignee: Schering Corporation
    Inventors: David J. Blythin, Ho-Jane Shue, Ashit K. Ganguly
  • Patent number: 4987138
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, 1-mercapto C.sub.2-7 alkyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl(NOH) or --C(C.sub.1-6 alkyl)NNH.
    Type: Grant
    Filed: August 11, 1988
    Date of Patent: January 22, 1991
    Assignee: Beecham Group p.l.c.
    Inventors: Frederick Cassidy, Geoffrey Stemp
  • Patent number: 4981980
    Abstract: Fermentation of a nutrient medium by a Hypomycetes fungus of the genus Memnoniella or Stachybotrys yields a product with a major component of structural formula I: ##STR1## which is an inositol monophosphate phosphatase inhibitor and thereby useful in the treatment of manic depression.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: January 1, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Robert A. Giocobbe, Leeyuan Huang, Yu L. Kong, Yiu-Kuen T. Lam, Sagrario M. Del Val, Carol F. Wichmann, Deborah L. Zink
  • Patent number: 4925479
    Abstract: Compounds of the formula ##STR1## wherein X is oxy, thio, sulfinyl or sulonyl;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; andR.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 aloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: May 15, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventor: David L. Lee
  • Patent number: 4910323
    Abstract: 2'-substituted-spiro[benzofuran-2(3H),1'-cyclohexanes] and methods of preparing same are described. On the aromatic portion of the benzofuran ring, there may be a substituent or substituents including halogen, amino, lower-alkyl-substituted amino, lower alkyl, lower alkoxy, hydroxy and nitro. The substituents at the 2-position of the cyclohexane ring are --(CH.sub.2).sub.n NR.sup.1 R.sup.2 where n is 0, 1 or 2 and R.sup.1 and R.sup.2 are each independently hydrogen and alkyl of 1-3 carbons. These compounds are useful as antidepressants and analgesics.Various other compounds which are useful as intermediates for preparing the aforementioned compounds and methods for preparing same are also described.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: March 20, 1990
    Assignee: Hoechst Roussel Pharmaceuticals, Inc.
    Inventors: Edward J. Glamkowski, Michael C. Jones
  • Patent number: 4904814
    Abstract: Process for the preparation of tert-alkyl esters of the formula I ##STR1## in which m is 1 or 2, R is C.sub.4 -C.sub.12 tert-alkyl and X, if m=1, is unsubstituted or halogen-substituted alkyl, cycloalkyl, unsubstituted or substituted aryl or aralkyl, or an aromatic heterocyclic radical and, if m=2, is a direct bond, --CH.sub.2).sub.n, in which n can be an integer from 1 to 8, or 1,2-, 1,3- or 1,4-phenylene, by reaction of an ester of the formula II ##STR2## in which R.sub.1 is methyl or ethyl, with an alcohol ROH in the presence of a catalyst customary for transesterifications.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: February 27, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Urs Frei, Rudolf Kirchmayr
  • Patent number: 4853410
    Abstract: Racemic and chiral (2R,4R)-4-c-hydroxy-2-4-(substituted)chroman(and thiochroman)-4-acetic acids and their pharmaceutically acceptable salts, their use in the treatment of diabetic complications and intermediates therefor.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: August 1, 1989
    Assignee: Pfizer Inc.
    Inventor: Christopher A. Lipinski
  • Patent number: 4826977
    Abstract: A series of novel photochromic spiropyrans are disclosed in which a spiro-adamantane group is introduced into the 2-position of the benzopyran or naphthopyran ring. The spiropyran compounds of the invention exhibit heliochromic properties, i.e. they color in sunlight and fade rapidly at ambient temperatures in the absence of U.V. light, making them good candidates for use in the manufacture of sunglasses. The invention includes lenses which darken in sunlight and incorporate the novel spiropyrans and a process for the preparation of the spiropyran compounds.
    Type: Grant
    Filed: May 15, 1987
    Date of Patent: May 2, 1989
    Assignee: The Plessey Company plc
    Inventors: Harry G. Heller, Stephen N. Oliver, John Whittall, Ian Tomlinson
  • Patent number: 4782083
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: one of R.sub.1 and R.sub.2 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl or R.sub.1 and R.sub.2 together are C.sub.2-5 -polymethylene;either R.sub.3 is hydrogen, hydroxy, C.sub.1-6 alkoxy or C.sub.1-7 acyloxy and R.sub.4 is hydrogen or R.sub.3 and R.sub.4 together are a bond;R.sub.5 is hydrogen C.sub.1-6 alkyl optionally substituted by halogen hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkoxycarbonyl, carboxy or amino optionally substituted by one or two independent C.sub.1-6 alkyl groups, or C.sub.2-6 alkenyl, amino optionally substituted by a C.sub.1-6 alkyl or C.sub.1-6 alkenyl group or by a C.sub.1-6 alkanoyl group optionally substituted by up to three halo atoms, by a phenyl group optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halogen, or aryl or hetroaryl, either being optionally substituted by one or more groups or atoms selected from the class of C.sub.1-6 alkyl, C.sub.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: November 1, 1988
    Assignee: Beecham Group P.L.C.
    Inventors: Frederick Cassidy, Geoffrey Stemp, John M. Evans
  • Patent number: 4737493
    Abstract: Substituted phenoxy-, 1-, and 2-naphthalenyloxy-, indenyl-, indolyl-, benzofuranyl-, and benzo[b]thiofuranylcarboxamides of 7,8-(substituted-diamino)-1-oxaspiro[4.5]decanes are useful as analgesic agents.A method of making the compounds, pharmaceutical compositions employing the compounds, and a method of alleviating pain in warm-blooded animals are also disclosed.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: April 12, 1988
    Assignee: Warner-Lambert Company
    Inventor: David C. Horwell
  • Patent number: 4687779
    Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl,C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, C.sub.1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.2 is nitro, cyano or C.
    Type: Grant
    Filed: August 29, 1984
    Date of Patent: August 18, 1987
    Assignee: Beecham Group p.l.c.
    Inventor: John M. Evans
  • Patent number: 4677116
    Abstract: Compounds of formula (I) ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkylthiocarbonyl, C.sub.1-6 alkoxythiocarbonyl, C.sub.1-6 alkylthiocarbonyloxy, C.sub.1-6 alkylthiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.
    Type: Grant
    Filed: October 12, 1984
    Date of Patent: June 30, 1987
    Assignee: Beecham Group p.l.c.
    Inventor: John M. Evans
  • Patent number: 4670041
    Abstract: Compounds of the formula ##STR1## wherein X is (--CR.sub.4 R.sub.4 --).sub.m in which m is 0 or 1;Y is (--CR.sub.5 R.sub.6 --).sub.n in which n is 0, 1 or 2;Z is (--CR.sub.7 R.sub.7 --).sub.p in which p is 1, 2, or 3; the sum of m+n+p is an integer of 2 to 5, inclusive;R.sub.2 and R.sub.3 each is H or alkyl, and the like;R.sub.1 is H or alkyl; andW is an unsaturated moiety, are useful as plant growth regulators and herbicides.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: June 2, 1987
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: George B. Payne, Samuel B. Soloway, James E. Powell, Steven A. Roman, Willy D. Kollmeyer
  • Patent number: 4659737
    Abstract: Substituted benzopyrans of the formula ##STR1## in which --A-- is a single or double bond,X is a direct bond, optionally substituted methylene, oxygen or optionally substituted --NH--, and the various other radicals can have various meanings,or pharmaceutically acceptable addition salts thereof, which possess anti-hypertensive activity.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: April 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Kabbe, Ulrich Niewohner, Arno Widdig, Andreas Knorr, Bernward Garthoff, Stanislav Kazda
  • Patent number: 4647579
    Abstract: Novel substituted 4-hydroxy-benzopyrans of the formula ##STR1## in which X is a single bond, ##STR2## and the other radicals can have various meanings, or pharmaceutically acceptable addition salts thereof, which are active on the circulation system.
    Type: Grant
    Filed: March 21, 1985
    Date of Patent: March 3, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Kabbe, Arno Widdig, Ulrich Niewohner, Andreas Knorr, Bernward Garthoff, Stanislav Kazda
  • Patent number: 4644070
    Abstract: Anti-hypertensive compounds of formula (I): ##STR1## wherein: one of R.sub.1 and R.sub.2 is nitro, cyano or C.sub.1-3 alkylcarbonyl, and the other is methoxy or amino optionally substituted by one or two C.sub.1-6 alkyl or by C.sub.2-7 alkanoyl;one of R.sub.3 and R.sub.4 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl, or R.sub.3 and R.sub.4 together with the carbon atom to which they are attached are C.sub.3-6 spiroalkyl;R.sub.5 is hydrogen, C.sub.1-3 alkyl or C.sub.1-8 acyl; andn is 1 or 2; the lactam group being trans to the OR.sub.5 group; or, when the other of R.sub.1 and R.sub.2 is amino, a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: December 18, 1984
    Date of Patent: February 17, 1987
    Assignee: Beecham Group p.l.c.
    Inventors: John M. Evans, Robin E. Buckingham, Kenneth Willcocks
  • Patent number: 4629734
    Abstract: Compounds of formula (I): ##STR1## wherein: R.sub.1 -R.sub.6 are as defined in the specification;X is oxygen or sulphur; and the R.sub.6 NCXR.sub.5 and OCOH moieties are trans and, when one or the other of R.sub.1 and R.sub.2 is an amino group, pharmaceutically acceptable salts thereof, a process and intermediates for preparing them, pharmaceutical compositions containing them, and their use in the treatment of mammals.
    Type: Grant
    Filed: May 16, 1984
    Date of Patent: December 16, 1986
    Assignee: Beecham Group p.l.c.
    Inventor: Valerie A. Ashwood
  • Patent number: 4623657
    Abstract: There are described compounds of the formula ##STR1## where each X is independently H, halogen, loweralkyl, loweralkoxy or OH; m is 1 or 2; and R is --H, .dbd.O, ##STR2## .dbd.CH(CH.sub.2).sub.n NR.sub.1 CH.sub.3, --CH.sub.2 (CH.sub.2).sub.n NR.sub.1 R.sub.2, .dbd.N--OH, .dbd.N--OCH.sub.2 (CH.sub.2).sub.n NR.sub.1 R.sub.3, ##STR3## .dbd.N--OCH.sub.2 CHOHCH.sub.2 NR.sub.1 R.sub.3, --NR.sub.2 R.sub.3, --OH or --OCH.sub.2 (CH.sub.2).sub.n NR.sub.1 R.sub.2, n being 1 or 2, R.sub.1 being loweralkyl, R.sub.2 being H, loweralkyl, loweralkanoyl, arylloweralkyl, arylloweralkanoyl, diarylloweralkyl, diarylloweralkanoyl, --CO.sub.2 C.sub.2 H.sub.5 or --CN, and R.sub.3 being H, loweralkyl, arylloweralkyl or diarylloweralkyl, or a pharmaceutically acceptable acid addition salt thereof, which are useful as antihypertensive, anticonvulsant, analgesic and antidepressant agents.
    Type: Grant
    Filed: September 5, 1985
    Date of Patent: November 18, 1986
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Edward J. Glamkowski, Frederick J. Ehrgott, Jr.
  • Patent number: 4594435
    Abstract: 2'-substituted-spiro[benzofuran-2(3H),1'-cycloalkanes] and methods of preparing same are described. On the aromatic portion of the benzofuran ring, there may be a substituent or substituents including halogen, amino, lower-alkyl-substituted amino, lower alkyl, lower alkoxy, hydroxy and nitro. The substituents at the 2-position of the cycloalkane ring are --(CH.sub.2).sub.n NR.sup.1 R.sup.2 where n is 0, 1 or 2 and R.sup.1 and R.sup.2 are each independently hydrogen and alkyl or 1-3 carbons. These compounds are useful as antidepressants and analgesics.Various other compounds which are useful as intermediates for preparing the aforementioned compounds and methods for preparing same are also described.
    Type: Grant
    Filed: February 28, 1985
    Date of Patent: June 10, 1986
    Assignee: Hoechst-Roussel Pharmaceuticals, Inc.
    Inventors: Edward J. Glamkowski, Michael C. Jones, deceased
  • Patent number: 4581166
    Abstract: A process is proposed for the isolation and purification of antibiotics wherein an antibiotic containing solution is extracted with an extraction agent at a temperature of from 0.degree. to 40.degree. C. and at a pressure which lies between the critical pressure and the ten-fold value of the critical pressure of the extraction agent, with the weight ratio of antibiotic containing solution to the extraction agent being 1:5 to 1:20, wherein the antibiotics are precipitated from the antibiotic containing extraction agent by reducing its density and wherein the extraction agent is recirculated. An entrainer may be added to the extraction agent. The reduction in density of the antibiotic containing extraction agent may be effected by expansion to a pressure of from 30 to 70 bar.
    Type: Grant
    Filed: May 11, 1984
    Date of Patent: April 8, 1986
    Assignee: Fried. Krupp Gesellschaft mit beschrankter Haftung
    Inventors: Siegfried Peter, Hubert Coenen, Rainer Hagen
  • Patent number: 4575511
    Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, C.sub.1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkoxysulphinylamino, C.sub.1-6 alkoxysulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or one of R.sub.1 and R.sub.2 is nitro, cyano or C.sub.
    Type: Grant
    Filed: May 16, 1984
    Date of Patent: March 11, 1986
    Assignee: Beecham Group p.l.c.
    Inventors: John M. Evans, Frederick Cassidy
  • Patent number: 4571406
    Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, 1-mercapto C.sub.2-7 alkyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino, or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.
    Type: Grant
    Filed: May 16, 1984
    Date of Patent: February 18, 1986
    Assignee: Beecham Group p.l.c.
    Inventors: John M. Evans, Frederick Cassidy
  • Patent number: 4568692
    Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, C.sub.1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or -C(C.sub.1-6 alkyl)NOH or -C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.
    Type: Grant
    Filed: May 15, 1984
    Date of Patent: February 4, 1986
    Assignee: Beecham Group p.l.c.
    Inventor: John M. Evans
  • Patent number: 4563458
    Abstract: The invention relates to substituted 4-aminomethylene-chromans and chromens of Formula (I) infra, as well as methods for making of said chromans and chromens, compositions containing said chromans and chromens and methods for the use of said chromans, chromens and compositions containing said chromans and chromens. The compounds and compositions of the invention are useful for their circulation influencing activity.
    Type: Grant
    Filed: December 13, 1983
    Date of Patent: January 7, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Arno Widdig, Hans-Joachim Kabbe, Andreas Knorr, Ulrich Benz
  • Patent number: 4558068
    Abstract: Novel spirobenzofuranone compounds of the formula: ##STR1## wherein R is a hydrogen atom or a lower alkyl and --X-- is ##STR2## and a pharmaceutically acceptable salt thereof, have gastric secretion inhibitive, antiulcer activities, and are of value as drugs.
    Type: Grant
    Filed: July 12, 1984
    Date of Patent: December 10, 1985
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirosada Sugihara, Masazumi Watanabe, Mitsuru Kawada, Isuke Imada
  • Patent number: 4555509
    Abstract: Compounds of the formula (I): ##STR1## wherein: one of R.sub.1 and R.sub.2 is hydrogen and the other is C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, 1-mercapto C.sub.2-7 alkyl or formyl;one of R.sub.3 and R.sub.4 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl, or R.sub.3 and R.sub.4 together with the carbon atom to which they are attached are C.sub.3-6 spiroalkyl;R.sub.5 is hydrogen, C.sub.1-3 alkyl or C.sub.1-8 acyl; andn is 1 or 2; the lactam group being trans to the OR.sub.5 group, having anti-hypertensive activity.
    Type: Grant
    Filed: March 22, 1984
    Date of Patent: November 26, 1985
    Assignee: Beecham Group p.l.c.
    Inventors: John M. Evans, Robin E. Buckingham, Kenneth Willcocks
  • Patent number: 4517311
    Abstract: 2'-Substituted-spiro[benzofuran-2(3H),1'-cycloalkanes] and methods of praparing same are described. On the aromatic portion of the benzofuran ring, there may be a substituent or substituents including halogen, amino, lower-alkyl-substituted amino, lower alkyl, lower alkoxy, hydroxy and nitro. The substituents at the 2-position of the cycloalkane ring are --(CH.sub.2).sub.n NR.sup.1 R.sup.2 where n is 0, 1 or 2 and R.sup.1 and R.sup.2 are each independently hydrogen and alkyl of 1-3 carbons. These compounds are useful as antidepressants and analgesics.Various other compounds which are useful as intermediates for preparing the aforementioned compounds and methods for preparing same are also described.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: May 14, 1985
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Edward J. Glamkowski, Michael C. Jones, deceased, by Herbert Jones, administrator
  • Patent number: 4497820
    Abstract: Substituted imino derivatives of 4 H-2, 3-dihydrobenzopyran and 4 H-2, 3-dihydrobenzothiopyran, and pharmaceutical compositions containing them. The compounds are active on the central nervous system, in particular as central nervous system depressants, i.e., sedatives, anticonvulsive agents, tranquilizers and sleep-inducing agents.
    Type: Grant
    Filed: May 4, 1983
    Date of Patent: February 5, 1985
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Lucio Merlini, Alessandro Rossi, Metilde Buonamici
  • Patent number: 4481214
    Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, C.sub.1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.
    Type: Grant
    Filed: May 19, 1983
    Date of Patent: November 6, 1984
    Assignee: Beecham Group p.l.c.
    Inventor: John M. Evans
  • Patent number: 4479007
    Abstract: Chroman-4-ones are prepared by reacting an o-hydroxyarylcarbonyl compound with a carbonyl compound in the presence of an amine.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: October 23, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Kabbe
  • Patent number: 4446113
    Abstract: Compounds of formula (I): ##STR1## wherein: one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, alkylsulphinyl, alkylsulphonyl, alkoxysulphinyl, alkoxysulphonyl, alkylcarbonylamino, alkoxycarbonylamino, or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two alkyl groups, or alkylsulphinylamino, alkylsulphonylamino, alkoxysulphinylamino or alkoxysulphonylamino, or ethylenyl terminally substituted by alkylcarbonyl, nitro or cyano or --C(alkyl)NOH or --C(alkyl)NNH.sub.2, the alkyl groups or alkyl moieties of alkyl-containing groups having from 1 to 6 carbon atoms;one of R.sub.3 and R.sub.4 is hydrogen or alkyl having from 1 to 4 carbon atoms and the other is alkyl having from 1 to 4 carbon atoms, or R.sub.3 and R.sub.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: May 1, 1984
    Assignee: Beecham Group p.l.c.
    Inventors: John M. Evans, Robin E. Buckingham, Kenneth Willcocks
  • Patent number: 4415741
    Abstract: Chroman-4-ones are prepared by reacting an o-hydroxyarylcarbonyl compound with a carbonyl compound in the presence of an amine.
    Type: Grant
    Filed: January 7, 1982
    Date of Patent: November 15, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Kabbe
  • Patent number: 4404221
    Abstract: 2'-Substituted-spiro[benzofuran-2(3H),1'-cyclohexanes] and methods of preparing same are described. On the aromatic portion of the benzofuran ring, there may be a substituent or substituents including halogen, amino, lower-alkyl-substituted amino, lower alkyl, lower alkoxy, hydroxy and nitro. The substituents at the 2-position of the cyclohexane ring are --(CH.sub.2).sub.n NR.sup.1 R.sup.2 where n is 0, 1 or 2 and R.sup.1 and R.sup.2 are each independently hydrogen and alkyl of 1-3 carbons. These compounds are useful as antidepressants and analgesics.Various other compounds which are useful as intermediates for preparing the aforementioned compounds and methods for preparing same are also described.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: September 13, 1983
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Edward J. Glamkowski, Michael C. Jones
  • Patent number: 4333759
    Abstract: The invention provides herbicidally-active 2,3-dihydro-5-cyanobenzofurans of the formula: ##STR1## (wherein: R.sup.1 and R.sup.2 together represent .dbd.O or R.sup.1 represents hydrogen and R.sup.2 represents hydrogen, hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, alkylthiocarbonyloxy, halogen, isothiocyanato, amino, alkylamino, dialkylamino, arylamino, acylamino, alkoxycarbonylamino, alkylthiocarbonylamino, N-bonded heterocyclyl, cyano or alkylthio; R.sup.3 and R.sup.4 together represent alkylene or each represent hydrogen or alkyl; and R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, each represent hydrogen, halogen, alkyl, alkoxy, acyl or cyano), processes for their preparation and herbicidal compositions containing them.
    Type: Grant
    Filed: December 4, 1980
    Date of Patent: June 8, 1982
    Assignee: Fisons Limited
    Inventors: Peter S. Gates, Derek Baldwin, Carol A. Wilson, John Gillon
  • Patent number: 4330554
    Abstract: Novel spirobenzofuranone compounds of the formula: ##STR1## have gastric secretion inhibitive, antiinflammatory and analgesic activities, and are of value as drugs.
    Type: Grant
    Filed: April 17, 1981
    Date of Patent: May 18, 1982
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirosada Sugihara, Masazumi Watanabe, Mitsuru Kawada, Isuke Imada